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Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Group Migration in AziridinesLi
15 examples.
HODGSON, D.M.; HMPHREYS, P.G.; XU, Z.; WARD, G.
GP
R
N
PG
R
N
H
PGLTMP (3-5 eq.)
THF, -78°C, 90min
PG=CO2tBu, 67-90%PG=PO(OEt)2, 79-95%
Angew. Chem. Int. Ed. 2245 22482007 46 -, , 13 ,
Unusual Reaction of 1-Alkyl-2-(bromomethyl)aziridines with MethyllithiumLi
D’HOOGHE, M.; DE KIMPE, N.
MVI
N
R
BrMe
NH
R
Me
HC CHN
R N
R
Br N
R
N
R2-3 equiv. MeLi
THF or Et2O, 0°C
0° - rt, 18-20h
-
60-75%R = iPr, t-Bu, CHEt2
Chem. Commun. 1275 12772007 -, , 12 ,
Bi-Phenyls and Bi-Naphtyls DerivativesLi
SOLINAS, M.; MEADOWS, R.E.; WILSON, C.; BLAKE, A.J.; WOODWARD, S.
GP
CH3OH
O
SiPh2
1. n-BuLi-TMEDAEt2O, 0°C, 24h
2. Cl2SiPh2
binaphtyl, 55%biphenyl, 60%
Eur. J. Org. Chem. 1613 16232007 -, , 10 ,
αααα-Chloro-ββββ-ethoxyethenyllithium ReagentsLi
ITOH, A.; SAKAI, M.; YOSHIMATSU, M.
CC
(Het)ArH
Cl
OEt
(Het)ArLi
Cl
OEt
(Het)Ar
Cl
OEt
R
OHR'
R"
R'
R
O
(Het)ArnBuLi (1 eq), -78°C
THF, 10 min.
RCOR' (0.67 eq)THF, 10 min.
then H2O
16 Examples Yields = 30 - 98%
Pd
Eur. J. Org. Chem. 2006 20142007 -, , 12 ,
1
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Well-Defined OligothiophenesLi
This process is better than thermal elimination that gives undefined polymers
ZHANG, F.; BAÜERLE, P.
GP
SS
S
Bu Bu
SS
S
Bu Bu
L2PtS
SS
Bu Bu
SS
S
Bu Bu
SS
S
Bu Bu
1. n-BuLi (1 eq.), THF-78°C to 0°C
2. L2PtCl2 (0.5 eq.)THF, -78°C to r.t.
oxidation
chemical or electrochemical
Pt
J. Am. Chem. Soc. 3090 30912007 129 -, , 11 ,
Application of Lithio SilolesLi
WANG, C.; LUO, Q.; SUN, H.; GUO, X.; XI, Z.
GP
LiLi
SiMe3
SiMe3
Ph
Ph
SiMe3
Li
Ph
PhSiMe2
SiMe3
FG
Ph
PhSiMe2
HMPA,
ether, reflux
electrophile
70-90%
7 examples
J. Am. Chem. Soc. 3094 30952007 129 -, , 11 ,
Stereoselective LithiationLi
Calculations support the higher stability of the syn arrangement for the lithio intermediate.
KESSAR, S.V.; SINGH, P.; SINGH, K.N.; VENUGOPALAN, P.; KAUR, A.; BHARAVAM, P.V., SHARMA, A.K.
GP
N
H
BF3
N
H
BF3
H
Li
N
H
BF3
Li
H
N
H
BF3
H
C(OH)Ph2
N
H
BF3
C(OH)Ph2H
+
syn anti
s-BuLi-TMEDA
Et2O, -78°C
Ph2CO
97% 3%
46%
J. Am. Chem. Soc. 4506 45072007 129 -, , 15 ,
Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides and ChlorohydrinsLi
Methodology applied to the synthesis of (+)-β-cuparenoneHODGSON, D. M.; CHUNG, Y. K.; NUZZO, I.; FREIXAS, G.; KULIKIEWICZ, K. K.; CLEATOR, E.; PARIS, J.-M.
MVI
O
OHCl
OLi
NLi
OH
or
J. Am. Chem. Soc. 4456 44622007 129 -, , 14 ,
2
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Homologation of Pinacol Boronates by Enantioenriched Chloroalkyllithium ReagentsLi
Iterative stereospecific reagent-controlled homologation
BLAKEMORE, P. R.; BURGE, M. S.
MVI
O
OB
Bn
ClLi
Bn
O
O
B
Bn
Cl
Bn
Li
O
OB
BnBn
ClLi ClLi
Bn
O
OB
BnBn
Bn
er = 99:1
B
J. Am. Chem. Soc. 3068 30692007 129 -, , 11 ,
Lithiothiophene-2-carboxylatesLi
GANNON, M. K.; DETTY, M. R.
CC
S CO2H
Br
S CO2Li
Li
X
O
Me2N NMe2
XMe2N NMe2
S CO2H
+
-
3- or 5-Br
tBuLi (2.1 eq), THF,
TMEDA (0.25 eq), -78°C
3- or 5-Li
X = O, S, Se
THF, RT then reflux, 12h
(0.25 eq)i)
ii) AcOH (2.1 eq), then HPF6aq
PF6
J. Org. Chem. 2647 26502007 72 -, , 7 ,
Aggregation of Alkyllithiums in THFLi
Computed studies (solvatation number, aggregation state, ...) are reported.
PRATT, L. M.; TRUHLAR, D. G.; CRAMER, C. J.; KASS, S. R.; THOMPSON, J. D.; XIDOS, J. D.
CC
O
OR Li
O
R Li O
O
OLiR
RLiO tetramer
J. Org. Chem. 2962 29662007 72 -, , 8 ,
Pyramidalized AlkeneLi
FORMAN, M. A.; MORAN, C.; HERRES, J. P.; STAIRS, J.; CHOPKO, E.; POZZESSERE, A.; KERRIGAN, M.; KELLY, C.;LOWCHYJ, L.; SALANDRIA, K.; GALLO, A.; LOUTZENHISER, A.
CC
II
LiI
O
Me
Me
OMe Me
Diels AlderCycloaddition 3 Examples
Yields = 13 - 45%for example :
-LiInBuLi (1.2 eq), THF, -78°Cthen 0°C, 2h
ortBuLi (1.7 - 3 eq), -78°C, heptane/Et2O : 20/1then 0°C, 2h
J. Org. Chem. 2996 30052007 72 -, , 8 ,
3
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Enantioselective Synthesis of (-)-Hennoxazole ALi
SMITH, T. E.; KUO, W.-H.; BOCK, V. D.; ROIZEN, J. L.; BALSKUS, E. P.; THEBERGE, A. B.
CC
O
O
N
N
O
TBS
Me
OTBS
MeH
OMe
MeOO
O
N
N
O
OH
MeH
OMe
MeO
Me
MeMe
Br
Me
MeMe
i) LiNEt2, THF, -78°C
ii)
iii) TBAF, THF (-)-Hennoxazole A
Org. Lett. 1153 11552007 9 -, , 6 ,
Lithiation of N-Alkyl-2,3-diphenylaziridinesLi
High diastereoselectivity is reported. Solvent effect is investigated.
LUISI, R.; CAPRIATI, V.; FLORIO, S.; MUSIO, B.
CC
N
R
Ph
PhN
R
Ph
Ph EN
R
E
Ph Ph
sBuLi, TMEDAhexane or toluene
-78°C, 3 - 4hthen Electrophile
sBuLi, THF,-78°C, 3 - 4h
then Electrophile
R = alkyl 8 examplesYields = 30 - 98%
10 examplesYields = 25 - 98%
Org. Lett. 1263 12662007 9 -, , 7 ,
Vinyl Lithiation of Cis-StilbeneLi
High stereoselectivity is reported.
COTTER, J.; HOGAN, A.-M. L.; O’SHEA, D. F.
CC
Ph
PhPh
Ph
Li
Ph
Li
Ph
Ph
Ph
EsBuLi (2 eq), PMDTA
THF, -25°C, 2h
Electrophile
7 Examples Yields = 32 - 76%
Org. Lett. 1493 14962007 9 -, , 8 ,
Rearrangement of Tritylamines by Phenyl or Aryl MigrationLi
THEODOROU, V.; SKOBRIDIS, K.; KARKATSOULIS, A.
CC
NH2RC6H4
PhPh
Ph2C N C6H4R
C NRC6H4
Ph Ph
.. C NRC6H4
Ph
Ph
..+
NCHPh
Ph
R
Li+
NCH
RC6H4Ph
Li+
nBuLi (1 eq),
THF, -75°C, 1h
R = Me, OMe, Br
- LiH
++
-
. .
-
. .
Tetrahedron 4284 42892007 63 -, , 20 ,
4
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
N-Alkenylations of HeterocyclesLi
C-Alkenylations of N-protected heterocycles using magnesium carbenoïds are reported too.
SAKURADA, J.; SATOH, T.
CC
R
R' Cl
MgCl
R
R'
MgCl
N
N
R
R'
E
N
R
R'
HN Li
N-Lithio heterocycles :
E+ (9 eq), CuI (cat)
-10°C to RT, 1h
7 ExamplesYields = 14 - 71%
10 ExamplesYields = 30 - 71%
-78°C to -10°Ctoluene, Et2O (9 eq)
(3 eq) NH4Cl
Mg
Tetrahedron 3806 38172007 63 -, , 18 ,
Anionic [4+2] CycloadditionLi
MAL, D.; SENAPATI, B. K.; PAHARI, P.
CC
N
O
O
X
P
N
P
R
EO
O
X Li
E
R
N
H
OY
W
Y
W
O
X = H or SO2Ph
LDA (1 eq), -78°C
THF, 30 min. -40°C, THF, 15 min.then RT, 3h
or (1 eq)
or
P = Me, Bn
Tetrahedron 3768 37812007 63 -, , 18 ,
Hauser AnnulationLi
The reaction failed with a more sterically demanding methoxy group instead of fluorine.
PAHARI, P.; SENAPATI, B.; MAL, D.
GP
O
F
O
SO2Ph
O O
FO
O
H
H
OHO
O
+t-BuOLi, THF
-60°C 84%
Tetrahedron Lett. 2635 26382007 48 -, , 14 ,
Access to 2-Fluoroalkyl IndolesMg
GE, F.; WANG, Z.; WAN, W.; HAO, J.
OS
N
Br
Me
CF3
ClN
Me
CF3
H
Mg, THF
0 °C - r.t., 2 h.82%
These nucleophilic substitutions have been demonstrated as the most efficient way to access new generation of interesting fluorine-containing indole derivatives.
Synlett 447 4502007 -, , 3 ,
5
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
One-Pot Double C-AcylationMg
Double intermolecular C-acylation give the corresponding dicarbonyl compounds in good yields.
MATSUNAMI, M.; SAKAI, N.; MORIMOTO, T.; MAEKAWA, H.; NISHIGUCHI, I.
OS
O
Et Cl
OEt
Et O
+ 78%Mg
DMF
Synlett 769 7742007 -, , 5 ,
Cationic Alkyl Rare-Earth Metals Complexes for Dienes Living (Co)Polymerization.Sc
In-situ generated cations display outstanding performances in diene living polymerization and block copolymerization.
ZHANG, L.; SUZUKI, T.; LUO, Y.; NISHIURA, M.; HOU, Z.
GR
N
LnPPh2Ph2P
(THF)nMe3Si SiMe3
[HNMe2Ph][B(C6F5)4]
THF
N
LnPPh2Ph2P
THFTHF
Me3Si
[B(C6F5)4]
Ln= Sc (n=0), Y and Lu (n=1)
YLu
Angew. Chem. Int. Ed. 1909 19132007 46 -, , 11 ,
Arene Complexes of Organoscandium Cations.Sc
Arene displacement kinetic studies and reactivity towards diphenylacetylene are presented.
HAYES, P. G.; PIERS, W. E.; PARVEZ, M.
GR
N
NSc
Ar
Ar
Me
Me
[CPh3][B(C6F5)4]
Ar= 2,4,6-Me3C6H2
Rn
N
NSc
Ar
Ar
Me
Rn
[B(C6F5)4]
Chem. Eur. J. 2632 26402007 13 -, , 9 ,
Transesterification of Carboxylic EstersSc
A broad range of different functional groups was tolerated.
LE REMME, N.; KOSCHEK, K.; SCHNEIDER, C.
OS
O
OEt
O
OMe
Sc(OTf)391%
(1 mol%)
MeOH, 64 °C, 10 h
Synlett 491 4932007 -, , 3 ,
6
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Catalytic Diastereoselective AllylationY
DUEÑES, R.A.; MORKEN, J. P.
OS
O OBu
Me
Bu
SiMe3
O
Me
BuCH2Cl2, 22 °C.+
Y(OTf)3 or Sc(OTf)3(0.2 equiv.)
60%
d.r. (>20:1)
The allylation of Oshima–Utimoto products is an efficient process and, with appropriate substituents can provide highly functionalized and stereoselectived furans.
Sc
Synlett 587 5902007 -, , 4 ,
Rare-Earth Metals Tetraaluminate Derivatives.La
This study underlines the different alkylating power of rare-earth and aluminium methyl functions.
ZIMMERMANN, M.; TÖRNROOS, K. W.; ANWANDER, R.
GR
N
N NAr Ar
N
N NAr ArLa
Me MeMeMe
Al AlMe
MeMeMe
THF
-AlMe3(THF)N
N NAr ArLa
Me
Me
AlMe Me
O
THF
-THFN
N NAr ArLa
Me MeAl
MeMe
Ar=2,6-iPrC6H3
La(AlMe4)3
NdYAl
Angew. Chem. Int. Ed. 3126 31302007 46 -, , 17 ,
Catalytic Asymmetric Michael Malonate Addition to α,βα,βα,βα,β-Unsaturated N-Acylpyrroles.La
Ligand tuning affords good yields and enantioselectivity.
PARK, S.-Y.; MORIMOTO, H.; MATSUNAGA, S.; SHIBASAKI, M.
GR
O
RN
X
+Z
Z La(OiPr)3 (10%)
Ligand (10%)
O
N
X R
Z
Z
N
O
X = Z = CO2Bn 76-87% yield78-96% ee
7 examples
Ph
OH
O
HO
HOLigand:
Tetrahedron Lett. 2815 28182007 48 -, , 16 ,
SmI2-Mediated Saccharide CouplingSm
Synthesis of neuraminic acid disaccharide, precursor of oligosialic acids and gangliosides.
YUAN, X.; RESS, D. K.; LINDHARDT, R. J.
AS
OAc
OAcOAc
AcNHOAc
SO2Ph
CO2Me
OAll
OAll
Ac2N
OAll
SPh
CO2All
O
OAll
OAll
Ac2N
OAll
SPh
CO2All
OAc
OAcOAc
AcNHOAc
CO2Me
OH+
SmI2 (5 equiv.)
THF
35%, R/S 1/1
J. Org. Chem. 3085 30882007 72 -, , 8 ,
7
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Reactivity of Cyclopropanic δδδδ-Oxo-αααα,ββββ-Unsaturated Esters towards SmI2.Sm
Mechanistic pathways are discussed to account for the selectivity of the reaction.
CAMMOUN, C.; ZRIBA, R.; BEZZENINE-LAFOLLÉE, S.; GUIBÉ, F.
GR
O
CO2Me
PhPh
2.2 SmI2
4 tBuOH
PhPh
O
O
Tetrahedron 3728 37362007 63 -, , 18 ,
Samarium-Induced Reductive Cyclization in Natural Product Synthesis.Sm
Short synthesis of a lactone found in Greek tobacco is described.
CLARK, J. S.; HAYES, S.T.; BLAKE, A. J.; GOBBI, L.
GR
SmI2
MeOHOH
O
EtO2C OH
HO
EtO2C
HO
HH
OO
CH3
Tetrahedron Lett. 2501 25032007 48 -, , 14 ,
[3+2] Cycloaddition of N-Arylimines and EpoxidesYb
Novel synthetic method for the construction of five-membered heterocycles.
YU, C.; DAI, X.; SU, W.
OS
OCl N
H
ON
Cl
Yb(OTf)3 (10 mol%)
CH2Cl2, reflux+ 85%
Synlett 646 6482007 -, , 4 ,
Cycloaddition of AllenyltrimethylsilylthioketenesYb
Yb(OTf)3-catalyzed [4+2] cycloaddition of allenyltrimethylsilylthioketenes with arylaldimines
AOYAGI, S.; OHATA, S.; SHIMADA, K.; TAKIKAWA, Y.
OS
SMe3Si
Me NPh
N
S
Me3Si
Me PhBn
BnYb(OTf)3 (20 mol%)
CHCl3, reflux, 12 h.
+
(0.67 equiv.)
65%
Synlett 615 6182007 -, , 3 ,
8
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Total Synthesis of DiscodermolideTi
Other key step: Kocienski rearrangement (Cu)
DE LEMUS, E.; PORÉE, F.-H.; COMMERÇON, A.; BETZER, J.-F.; PANCRAZI, A.; ARDISSON, J.
BC
OO
OH
HO
OH O
OH
8
14
O SnBu3
OH
8
14
O
(iPr)2N
SnBu3
O
HO O
(iPr)2N
Discodermolide
Ti(OiPr)3
+
pentane/cyclohexane-78°C, 3h, 84%
SnCu
Angew. Chem. Int. Ed. 1917 19212007 46 -, , 11 ,
Metal Mediated Reactivity of Alkenynyl Carbamate: Ti vs LiTi
BOU CHEDID, R.; BRÜMMER, M.; WIBBELING, B.; FRÖHLICH, R.; HOPPE, D.
BC
OCb
PhOCb=
O
O
N(iPr)2
S= Sparteine
Ph
S.LiO
O
N(iPr)2
Ph
S.LiO
O
N(iPr)2
OCb
.
Ph OH
OCb
.
Ph OH
Ph
(OiPr)3Ti OCb
Ph
(OiPr)3Ti OCb
OCb
Ph
HO
OCb
Ph
HO
nBuLiS
1-
2-H2O
O
1-
2-H2O
O
crystallization15h, -78°C
81%ee 94%
61%ee 94%
1-
2-H2O
O
1-
2-H2O
O
ClTi(OiPr)3
inversion
ClTi(OiPr)3
inversion
Li
Angew. Chem. Int. Ed. 3131 31342007 46 -, , 17 ,
Regiodivergent Epoxide OpeningTi
Other examples
GANSAUER, A.; FAN, C.-A.; KELLER, F.; KEIL, J.
BPH
O
R'R
[Ti] 0.1 equiv
Mn, Coll•HCl1,4-C6H8
R'R
OH
R'R+
HO
[Ti] = )2TiCl2R = n-Pr, R' = (CH2)2CO2t-Bu
ee 80%
13% (ee 8%) 71% (ee 99%)
using ent-[Ti] 76% (ee 94%) 10% (ee 50%)
Mn
J. Am. Chem. Soc. 3484 34852007 129 -, , 12,
Coupling of Benzylic HalidesTi
BARRERO, A. F.; HERRADOR, M. M.; QUILEZ DEL MORAL, J. F.; ARTEAGA, P.; AKSSIRA, M.; EL HANBALI, F.;ARTEAGA, J. F.; DIEGUEZ, H. R.; SANCHEZ, E. M.
BPH
Y
XCp2TiCl (0.2 equiv)
Mn (8 equiv)THF, rt
R R
R
or R
R
(X = hal, Y = H) (X, Y = hal)
Mn
J. Org. Chem. 2251 22542007 72 -, , 6 ,
9
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Activation of Bis(pyrrolylaldiminato) Titanium Poly merization Catalysts with MAOTi
1H and 13C NMR investigation of the mechanism
BRYLIAKOV, K.P.; KRAVTSOV, E.A.; BROOMFIELD, L.; TALSI, E.P.; BOCHMANN, M.
AN
N
N
NPhTi
NPh
Cl
Cl
I
MAO*
Al:Ti = 10
N
N
NPhTi
NPh
Cl
13CH3
I2
MAO*
Al:Ti = 50
N
N
NPhTi
NPh
Cl
13CH3
+
MeMAO*_
C2H4 PE
MAO* = MAO-13CI3
Organometallics 288 2932007 26 -, , 2 ,
Synthesis and Structure of Titanatranes Containing Tetradentate Trianionic Donor LigandsTi
the complexes were tested in the ethylene polymerization reaction
PADMANABHAN, S.; KATAO, S.; NOMURA, K.
AN
Ti(OR')4 + [(HO-2,4-tBu2C6H2-6-CH2)2(HOCH2CH2)N]
N
O Ti O
OOR'
R
R
R
R
CH2Cl2 or tol
-30 to 25°C6h
R,R' = tBu,iPrR,R' = tBu,tBu
Organometallics 1616 16262007 26 -, , 7 ,
Biaryl Amidate Complexes in Catalytic Hydroamination/Cyclization of AminoalkenesTi
Hydroamination/cyclization of aminoalkenes: Structure-activity relantioships for group 4 complexes
GOTT, A.L.; CLARKE, A.J.; CLARKSON, G.J.; SCOTT, P.
AN
NH2H2N
2 RCOClEt3N
CH2Cl2
NHH
N
R
OO
R
TiBn4Me
Me
N
N O
R
O
R
TiBn
BnR = Me, Et, tBu, Mes
Zr
Organometallics 1729 17372007 26 -, , 7 ,
Primary tert-Alkylamines from NitrilesTi
TOMASHENKO, O.; SOKOLOV, V.; TOMASHEVSKIY, A.; DE MEIJERE, A.
BJL
R1CN
R2MgXTi(Oi-Pr)4R3MgX
NH2R2R1
R3
25-72%
Synlett 652 6542007 -, , 4 ,
10
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Synthesis of Tetraarylethenes via Cross McMurry CouplingTi
14 examples, yields: 59-80%.
DUAN, X.F.; ZENG, J.; LU, J.W.; ZHANG, Z.B.
GJ
C6H
4-pOH
Ph
Ph
PhO
Ph
PhO
p-HOC6H
4
Ph TiCl4-Zn-Pyr
+ 66%
(1.2 equiv)
(5 equiv)
THF, 25 h, reflux
Zn
Synthesis 713 7182007 -, , 5 ,
Catalytic Enantioselective Addition of Dimethylzinc to KetoneTi
FORRAT, V.J.; RAMON, D.J.; YUS, M.
TJ
Ph
O
Cl
Ti(OiPr)4
PhMe, 25 °CHOCSAC 5 mol%
+ Me2Zn PhCl
Me OH
HNNHO2S SO2
OHHO HOCSAC90%; ee 80%
Zn
Tetrahedron Asymm. 400 4052007 18 -, , 3 ,
Synthesis of αααα-Methylene-γγγγ-butyrolactonesTi
PAIRA, M.; BANERJEE, B.; JANA, S.; MANDAL, S.K.; ROY, S.C.
TJ
R
CHO
R
OO
CO2MeBr+
1. Cp2TiCl/THFrt, 5 h
2. 20% H2SO45-11 h
13 examples48-68%
Tetrahedron Lett. 3205 32072007 48 -, , 18 ,
Stereoselective Zr-mediated Ring ContractionZr
3 new C-C bonds and 3 new stereogenic centers are formed during this process
BARLUENGA, J.; AVAREZ-RODRIGO, L.; RODRIGUEZ, F.; FANANAS, F.J.; SORDO, T.L.; CAMPOMANES, P.
BC
Cp2ZrCl2
THF, -78°C1-
2-
-78°C to 25°C3- electrophile4- H+
OAr
MR
M= Li, MgBrR
OHAr
HE
R
E OH
Ar
0-56%
+
15-86%single diastereomer
14 examples
MgLi
Angew. Chem. Int. Ed. 2607 26092007 46 -, , 15 ,
11
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Reduction of Amides to Aldehydes. Scope and Mechanism.Zr
Many functional groups tolerated (esters, nitriles, nitro ...)
SPETSTOSER, J. T.; WHITE, J. M.; TUNOORI, A. R.; GEORG, G. I.
BPH
R N
OR'
R"
Cp2ZrHCl (1.2 equiv)
THF, 30 minR H
O
up to 99%
J. Am. Chem. Soc. 3408 34192007 129 -, , 11 ,
Gas-Phase Reactions of Bis(h5-Cp)methylzirconium Cations with Ketones and AldehydesZr
reactions in gas phase studied by Fourier transform ion cyclotron resonance mass spectrometry
AKSENOV, A.A.; CONTRERAS, C.S.; RICHARDSON, D.E.; EYLER, J.R.
AN
Cp2Zr CH3+
+ OCD3
CD3Cp2Zr
CH3+
OCD3
CD3
Cp2Zr
OCD3
CD3
H3C+
Cp2ZrCD3
+
OCH3
CD3
Organometallics 478 4882007 26 -, , 3 ,
1-Zircona-2-cyclohexenes: Novel Synthesis and Preliminary ReactionsZr
WANG, Q.; FAN, H.; XI, Z.
AN
I
R2R1 Cp2ZrHClTHF, r.t., 1h Cp2Zr
ICl 2eq. t-BuLi-78°C, 1h
Cp2Zr
R1 R2 H+ (or D+)-78°C
CH2
(D) H
R2R1
(D) H
Organometallics 775 7772007 26 -, , 4 ,
Generation of Heteroaromatic ZirconoceneZr
IKEUCHI, Y.; SAITOH, T.; TAGUCHI, T.; HANZAWA, Y.
TJ
XOR
TMS1. "Cp2Zr"
2. Cu(I) cat.
BrX
TMS
R
R9 examples
37-85%
Cu
Tetrahedron Lett. 2477 24802007 48 -, , 14 ,
12
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
N-C Bond Formation from CO2 and an Hf-based ComplexHf
BERNSKOETTER, W.H.; LOBKOVSKY, E.; CHIRIK, P.J.
BC
HfN
HfN
*Cp
*Cp
Cp*
Cp*
NN
OHfHf
O
O O
*CpCp* Cp*
Cp*
HfII
*Cp
*Cp
NN
OTMSTMSTMS
TMSO
O O
+TMSI
excess
2 CO2
Angew. Chem. Int. Ed. 2858 28612007 46 -, , 16 ,
Complexation of Bis(trimethylsilyl)acetylene by DecamethylhafnoceneHf
the first complexes of well-defined hafnium alkyne complexes with an intact alkyne
BEWERIES, T.; BURLAKOV, V.V.; BACH, M.A.; ARNDT, P.; BAUMANN, W.; SPANNENBERG, A.; ROSENTHAL, U.
AN
Cp*2HfCl2
LiMe3SiC2SiMe3
(tol.)
- 2 LiClCp*2Hf
SiMe3
SiMe3
Organometallics 247 2492007 26 -, , 2 ,
Hf Bis(phenoxyimino)dibenzyl Complexes. Their Activation toward Olefin PolymerizationHf
AXENOV, K.V.; KLINGA, M.; LEHTONEN, O.; KOSKELA, H.T.; LESKELA, M.; REPO, T.
AN
R1
R2
OH NR3
R1O
R2
Hf
NR3
Cl
Cl
2
1) BuLi or NaH in Et2O
2) HfCl4 in PhCH3
R1 = t-Bu, R2 = H, R3 = CH2PhR1 = R2 = cumyl, R3 = CH2PhR1 = t-Bu, R2 = H, R3 = C6F5R1 = R2 = cumyl, R3 = C6F5
Organometallics 1444 14602007 26 -, , 6 ,
Tantalum Phosphoniomethylidyne Complexes.Ta
Formation mechanism is proposed.
LI, X.; WANG, A.; WANG, L.; SUN, H.; HARMS, K.; SUNDERMEYER, J.
GR
TaCl Cl
ClCl
H2C PPh35Ta
C CCl
Ph3P
HPPh3
H2C PPh32Ta
CC
CPh3P
H
PPh3
HPPh3
-3 [Ph3PCH3]Cl - [Ph3PCH3]Cl
Organometallics 1411 14132007 26 -, , 6 ,
13
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Water-Soluble Organometallic Tantalum Derivatives.Ta
First examples of water-soluble organometallic tantalum species.
CONDE, A.; FANDOS, R.; OTERO, A.; RODRÍGUEZ, A.
GR
TaH3C
NO
O OTf
xs H2O
RT, 12 hrs TaH3C
NO
OOTfOH2
xs H2O
90°C, 30 min. TaHO
NO
OOTfOH2
Organometallics 1568 15702007 26 -, , 7 ,
Catalytic Enantioselective Methallylation of Aldehydes Cr
HARGADEN C.G.; MCMANUS H.A.; COZZI P.G.; GUIRY P.J.
AE
R H
O
BrR
OH
+
(i) CrCl3 (0.1 eq.), Mn (3 eq.)ligand (0.12 eq.), DIPEA (0.3 eq.)Me3SiCl, THF/CH3CN (7:1), 16h, RT
(ii) 1M HCl, THF*
yield : 41 to 92%ee : 33 - 95%R = Ph, p-MeO-Ph, p-Cl-Ph, C5H10, C6H13, Ph(CH2)2
NH
O
NBn
N
O
t-Bu
Ligand :
Mn
Org. Biomol. Chem. 763 7662007 5 -, , 5 ,
Epoxidation in Ionic Liquid.W
8 examples. Slight decrease of efficiency with the reycling.
KUMAR, A.
MJ
R2
R1
R3
[bmim]4[W10O23] (0.0036 eq.)
[bmim][BF4], 55 °C, 1.5-3 h
Conversion: 48-97%Selectivity: 74-95%
R2
R1
R3O
Catal. Commun. 913 9162007 8 -, , 6 ,
Oxidation of Alcohols Catalyzed by Mn-PorphyrinsMn
REZAEIFARD, A.; JAFARPOUR, M.; KARDAN MOGHADDAM, G.; AMINI, F.
PL
R1 R2
OH
R1 R2
OBu4NHSO5/CH3CN
Mn(TPP)OAc/Prrt
R1 = Aryl, allyl, alkylR2 = H, aryl, alkyl
80-98% yield
Bioorg. Med. Chem. 3097 31012007 15 -, , 8 ,
14
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Triaquatricarbonyl Cation and Its Conjugate BaseRe
Only with PF6-, both the cation and its conjugated base co-crystallized.
HERRICK, R. S.; ZIEGLER, C. J.; ÇETIN, A.; FRANKLIN, B. R.
HJR
Re COH2O
H2OOH2
OC CO
Re COH2O
H2OOH
OC CO
P
F
F
F F
FF
Eur. J. Inorg. Chem. 1632 16342007 -, , 12 ,
Hydrido Complexes with Polypyridine and Phosphonite LigandsRe
Extension to tolyl- and t-Butylacetylene, 69 and 73%, respectively.
ALBERTIN, G.; ANTONIUTTI, S.; CASTRO, J.; GARCIA-FONTAN, S.; SCHIPILLITI, G.
HJR
P = PPh(OEt)2
Green solid, 68%
+
[ReH2(bpy)P3]+ + xs HCCPh
ClCH2CH2Cl,reflux, 1 h
Re
N
N
P
P
PC
C
CC
H
H
HH
Ph
Ph
Eur. J. Inorg. Chem. 1713 17222007 -, , 12 ,
Mechanistic Insight into Hydrosilylation Reactions Catalyzed by Re ComplexesRe
The silane does not add across the metal-ligand multiple bond
DU, G.; FANWICK, P. E.; ABU-OMAR, M. M.
MVI
Re
O
ClPh3P Cl
ClH
SiEt3O
H
Ph
OPhSiEt3
H H
δ-
δ+
Si
J. Am. Chem. Soc. 5180 51872007 129 -, , 16 ,
A New Chiral Diiron Catalyst for Enantioselective EpoxidationFe
MARCHI-DELAPIERRE, C.; JORGE-ROBIN, A.; THIBON, A.; MÉNAGE, S.
LF
O
OCH3CO3HCH3CN / 0 °C / 2 min
O
OO
63%
FeO
Fe
N N
N N
N N
N N
*
*
*
*
X X
NN
*=
N NH H
bisPB
Chem. Commun. 1166 11682007 -, , 11 ,
15
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Acylnitroso Dienophile Generation Mediated by Metal Catalysis ProcessFe
46 exemples/conditions are described.
ADAMO, M. F. A.; BRUSHI, S.
DL
BocNHOH+ Diene Product
Mt (5mol%), Ligand (15 mol%)
H2O2, DCM or THF, rt20 to 11520 min
27-95% yield
Ligand: HOCH2CH2NH2, H2NCH2CH2NH2, Et3N
Mt: Fe(III), Cu(II), Cu(I), Ni(II), Ru(III)
Cu,Ru,Ni
J. Org. Chem. 2666 26692007 72 -, , 7 ,
Iron Carbonyl Mediated Spirocyclization Reactions: Dynamic DiastereoselectivityFe
PEARSON, A. J.; SUN, H.; WANG, X.
DL
PMBN
O
Bn
EtO2CFe(CO)3
+NPMB
O
Bn
CO2Et(OC)3Fe Benzene, CO,
350nm, 85°C,
72%PMBN
O
BnH
CO2Et Fe(CO)3
PMBNO
BnH
CO2Et Fe(CO)3
+
J. Org. Chem. 2547 25572007 72 -, , 7 ,
Iron-Catalyzed Arylmagnesiation of Aryl(alkyl)acetylenes Fe
YAMAGAMI, T.; SHINTANI, R.; SHIRAKAWA, E.; HAYASHI, T.
CS
Ar2MgBr
+
Ar1R
Fe(acac)3 (5 mol%)IPr( 20 mol%)
THF, 60°C, 16h
MgBrAr2
R Ar1
IPr14 examples, up to 91% yield
up to 95:5 E/Z
N N
Mg
Org. Lett. 1045 10482007 9 -, , 6 ,
Diastereoselective Ortho-Lithiation of Acetyl FerroceneFe
FERBER, B.; TOP, S.; HERSON, P.; JAOUEN, G.
BC
Fe Me
NMeO
tBu Fe Me
NMeO
tBu
I
Fe Me
OI
dr>95/5 73%(2 steps)
HClaq / THF
silica gel
1- tBuLi
2- THF
I
I
Li
Organometallics 1686 16912007 26 -, , 7 ,
16
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Synthesis of Nitrogen-Substituted FerrocenesFe
12 examples, yields: 31-84%.
OZCUBUKCU, S.; SCHMITT, E.; LEIFERT, A.. BOLM, C.
GJ
Fe
I
NH
Fe
N
+62%
CuI (1 equiv)
DMSO, 90°C, 18 h(2 equiv)
Cu
Synthesis 389 3922007 -, , 3 ,
Coupling of Cyclopropylcarbene–Chromium Complex with Ferrocenyl AlkynesFe
ZORA, M.; TUMAY, T. A.; BUYUKGUNGOR, O.
PL
OCH3
Cr(CO)5
Fe
R
1% aq. dioxane
100°C, 6h
O
OCH3
HO
Fc
HR
O
O
Fc
R
Fc = Ferrocene
R = CH3, 36% for 1, 17% for 2R = Bn, 16% for 1, 57% for 2R = Ph, 31% for 1, 55 for 2R = Fc, 18 for 1, 32 for 2
1 2
++
Cr
Tetrahedron 4018 40262007 63 -, , 19 ,
Biferrocene Diphosphine Ligand with only Planar ChiralityFe
The diphosphine ligand was used in Rh(I)-catalyzed asymmetric hydrogenation of β-keto sulfones.ZHANG, H.-L.; HOU, X.-L.; DAI, L.-X.; LUO, Z.-B.
PL
FePh2PFe
PPh2 OH
Fe
S
PPh2 OH3B
Fe
CHO
PPh2H3B
(R,R)
1) t-BuLi, THF, -78°C
2) + (R)-13) DABCO, toluene 60°C
(R)-1 89%
+
Rh
Tetrahedron Asymm. 224 2282007 18 -, , 2 ,
Planar Chiral Iridium Ferrocenyloxazolinylphosphine ComplexesFe
These complexes were applied as catalysts in the enantioselective hydrogenation of olefins.
LI, X.; LI, Q.; WU, X.; GAO, Y.; XU, D.; KONG, L.
PL
Fe
PPh2
N
O
R
Fe
PPh2
N
O R
Ir
+
X-1) [Ir(cod)Cl]2; 2) NaBArFor 1) [Ir(cod)Cl]2; 2) NaPF6
or 1) [Ir(cod)Cl]2
R = Me, i-Pr, t-Bu, PhX = BArF, PF6, Cl
Ir
Tetrahedron Asymm. 629 6342007 18 -, , 5 ,
17
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Ferrocenyl Substituted AziridinylmethanolsFe
The synthesized diastereomers has been used as ligands in enantioselective conjugate addition of diethylzinc to enones.
ISLEYEN, A.; DOGAN, O.
PL
Fe
O1) Br2
2)
NH2
Me PhH Fe
ON
H
Me PhH
S
S
S
S 54% + R 42%
Fe
OHN
H
Me PhH
S
SR
89% yield>99% de
L-selectrideTHF, -78°C
ZnNi
Tetrahedron Asymm. 679 6842007 18 -, , 5 ,
Cationic Iron-Catalyzed Intramolecular Hydroalkoxyl ation of OlefinsFe
KOMEYAMA, K.; MORIMOTO, T.; NAKAYAMA, Y.; TAKAKI, K.
PL
Ph
Ph
OHO
Ph
Ph
R1
R1 = H, CH3
R1
94-97%
hydroxyolefin (0.5 mmol)FeCl3 (10 mol%)
AgOTf (30 mol%), DCE (5 mL)80°C
Tetrahedron Lett. 3259 32612007 48 -, , 18 ,
Synthesis of Multifunctionalized 1,2,4-Triazolidines via Three Component CouplingRu
R1, R2: aryl; catalyst: ruthenium porphyrin.
WANG, M.-Z.; HAI-WEI XU, H.-W.; LIU, Y.; WONG, M.-K.; CHE, C.-H.
AF
R1 NR2 N N
EtOOC
Cl
N2
OR*
O [Ru(2,6-Cl2TPP)(CO)](1 mol %)
ClCH2CH2Cl45 °C, 12 h
10 - 64 %, 21 - 84 % de
EtOOC COOEt
R2R1
OR*
O
* *+ +
Ph
R*=
Adv. Synth. Catal. 2391 23962006 348 -, , 16-1
,
Repetitive Application of a Fluorous Chiral BINAP–Ru ComplexRu
A trisperfluoroalkylsilyl-modified (S)-BINAP ligand has been prepared.
HORN, J.; BANNWARTH, W.
LF
R1
R2
O
O Ru-RF-BINAPFSG
10-30 bar H260 °C
R1
R2
O
O
H
*
RF-BINAP:(RF)3Si
(RF)3Si
PPh2PPh2
RF = CH2CH2C8F17
Eur. J. Org. Chem. 2058 20632007 -, , 13 ,
18
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
RuCl2(dmso)4 Catalyzes the Solvent-Free Indirect Friedländer Synthesis of QuinolinesRu
MARTINEZ, R.; RAMÓN, D. J.; YUS, M.
LF
NH2
X
R2
R1
R3
XR4
RuCl2(dmso)4
KOtBuPh2CO, solvent-free,100 °C
N
R2
R1R3
43-99%
Eur. J. Org. Chem. 1599 16052007 -, , 10 ,
Olefin Methathesis on ComplexesRu
X-Ray structure is given for each new product.
CHEN, W.-Z.; PROTASIEWICZ, J.D.; DAVIS, S.A.; UPDEGRAFF, J.B.; MA, L.-Q.; FANWICK, P.E.; REN, T.
GP
NAr
N
Ru
Ar
N Ru
Ar
ArCl
O
O
N
Ar
N
Ar
n
n
NAr
N
Ru
Ar
N Ru
Ar
ArCl
O
O
N
Ar
N
Ar
n
n
(Cy3P)2Cl2Ru(=CHPh) (5%)
CH2Cl2, reflux, overnight
Inorg. Chem. 3775 37822007 46 -, , 9 ,
Tandem Catalytic Carbene Addition/Bicyclization of EnynesRu
MONNIER, F.; VOVARD-LE BRAY, C.; CASTILLO, D.; AUBERT, V.; DÉRIEN, S.; DIXNEUF, P. H.; TOUPET, L.; IENCO,A.; MEALLI, C.
MF
XX R
Y
RRu
Cl
N2CHY[Ru] 5%
[Ru] =
J. Am. Chem. Soc. 6037 60492007 129 -, , 18 ,
Synthesis of Bridged PaclitaxelsRu
9 exemples, yields: 60-87%; study of paclitaxel-tubulin interactions.
GANESH, T.; YANG, C.; NORRIS, A.; GLASS, T.; BANE, S.; RAVINDRA, R.; BANERJEE, A.; METAFERIA, B.; THOMAS,S.L.; GIANNAKAKOU, P.; ALCARAZ, A.A.; LAKDAWALA, A.S. ; SNYDER, J.P.; KINGSTON, D.G.I.
GJ
O
R1O
O
O
O
XO
ONH
O OH
AcO OSiEt3
Ph
OBz
H
O
R1O
O
O
O
OO
NH
O OH
AcO OSiEt3
Ph
OBz
H
O
(H2IMes)(PCy
3)(Cl)
2Ru=CHPh
65%
CH2Cl2, rt, 4 h
J. Med. Chem. 713 7252007 50 -, , 4 ,
19
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Stereoselective Approach to Duprezianane, Polyquinane and Sterpunane FrameworkRu
SINGH, V.; PRAVEENA, G. D.; KARKI, K.; MOBIN, S. M.
DL
R1O
R
O
H
endo/exo mixtureDCM, rt, Grubb's I catalyst (4 mol%)R
1OO
R2 R2R: Me, R1: Me, R2: H 55%
R: H, R1: Me, R2: H 35%
R: Me, R1: H, R2: Me 49%
yield
J. Org. Chem. 2058 20672007 72 -, , 6 ,
Attenol A: Reductive Cyclyzation ApproachRu
LA CRUZ, T. E.; RYCHNOVSKY, S. D.
DL
OO OO
OO OO
2) H2, 100psi
93%
1) Grubb's II catalyst
cat.
RuPCy3
PhCl
ClNN MesMes
Cu,In,Rh
J. Org. Chem. 2602 26112007 72 -, , 7 ,
Enantioselective Synthesis of Gypsy Moth Pheromone DisparlureRu
PRASAD, K. R.; ANBARASAN, P.
DL
C10H21
OTs
OBn+
1) Grubb's II catalyst(5 mol%)
DCM, reflux, 6h, 92%
C10H21
OTs
OBn
2) H2, Pd/C, MeOH, rt, 3h, 90%
J. Org. Chem. 3155 31572007 72 -, , 8 ,
Total Synthesis and Bioactivity of an Unnatural Enantiomer of Merrilactone ARu
INOUE, M.; LEE, N.; KASUYA, S.; SATO, T.; HIRAMA, M.; MORIYAMA, M.; FUKUYAMA, Y.
DL
OH
HO
ODCBODCB
OH
HO
ODCBODCB
Grubb's I catalyst(0.1 equiv.)
DCM, reflux, 5h
ODCBODCB
OH
OH
Pb(OAc)4
85%
ODCBODCB
O
O
DCB: dichlorobenzyl
J. Org. Chem. 3065 30752007 72 -, , 8 ,
20
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
A Rapid and Simple Cleanup Procedure for Metathesis ReactionsRu
GALAN, B. R.; KALBARCZYK, K. P.; SZCZEPANKIEWICZ, S.; KEISTER, J. B.; DIVER, S. T.
CS
N N
RuPCy3
Cl
Cl
Ph
metathesis-active
MeOH, rt, 30 min
CNCH2CO2K N N
RuPCy3
ClC N CH2CO2KCNH2CKO2C
metathesis-inactive, easy to remove
Ph
Cl
Org. Lett. 1203 12062007 9 -, , 7 ,
Ru(II), Rh(III), Ir(III) for the Cyclometalation of Primary Benzyl AminesRu
SORTAIS, J.-B.; PANNETIER, N.; HOLUIGUE, A.; BARLOY, L.; SIRLIN, C.; PFEFFER, M.; KYRITSAKAS, N.
PG
RuCl
Cl
2 CAr-H
NH2
+ RuCAr
NH2NCCH3
PF6
NaOH, KPF6
CH3CN, rt, 72h
RhIr
Organometallics 1856 18672007 26 -, , 8 ,
Ru(II) for the Cyclometalation of Secondary Benzyl AminesRu
SORTAIS, J.-B.; PANNETIER, N.; CLÉMENT, N.; BARLOY, L.; SIRLIN, C.; PFEFFER, M.; KYRITSAKAS, N.
PG
RuCl
Cl
2 CAr-H
NHR
+ RuCAr
NHRNCCH3
PF6
NaOH, KPF6
CH3CN, rt, 72h
Organometallics 1868 18742007 26 -, , 8 ,
Base Free Synthesis of N-Heterocyclic Carbene Metal Complexes Ru
BLUM, A. P.; RITTER, T.; GRUBBS, R. H.
PG
N
N
C6F5
H
R
R
+ [M]PhCH3, 70°C N
N[M]
R
R
+ C6F5H
IrRh
Organometallics 2122 21242007 26 -, , 8 ,
21
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Spiro-Bridged bis(αααα-Amino Acid) Derivative Based on RCM ReactionsRu
ANDREI, M.; EFSKIND, J.; UNDHEIM, K.
PL
MeO2C
CO2Me
NHAc
AcHN
MeO2C
AcHN
NHAc
CO2Me
isomer ratio 3:2
NHAc
MeO2C
NHAc
CO2Me
Grubbs-II cat. (10%)
toluene, 85°C, 4h
73%
+
Tetrahedron 4347 43552007 63 -, , 20 ,
Synthesis of Cholaphanes by RCMRu
CZAJKOWSKA, D.; MORZYCKI, J. W.
PL
OH
O
O
O
O
OH
O
OH
OOH
OH
O
O
O
O
OHO
OH
O
OH
Grubbs I(25 mol%)
72%
E/Z = 8:1
Tetrahedron Lett. 2851 28552007 48 -, , 16 ,
Pd-Catalyzed Arylation/RCM Approach to AzabicyclesRu
MARTYNEZ-ESTYBALEZ, U.; SOTOMAYOR, N.; LETE, E.
PL
I
NH2
R1
NH2
R1 = CH2CH=CH2, CH=CHCH3, CH=CH2
R1SnBu3/[Pd]
PPh3
32-80%
R1
NMe
R2
Ph NMe Ph
( )n
n = 0,1,2
Grubbs' I or IIcatalysts
CH2Cl2, reflux
8-75%
1) PhCHO2) R2MgCl
3) LDA, MeI
R2 = CH2CH=CH2, CH=CH2
PdSnMg
Tetrahedron Lett. 2919 29222007 48 -, , 16 ,
Osmium(II) and Ruthenium(II) Arene Maltolato ComplexesOs
Rapid Hydrolysis and Nucleobase Binding (X-Ray, dynamic NMR studies, DFT calculations)
A.F.A. PEACOCK, M. MELCHART, R.J. DEETH, A. HABTEMARIAM, S. PARSONS, P.J. SADLER
CM
Os
O
OX
O
n+
X = Cl, n = 0X = OH2, n = 1X = OH, n = 0X = nucleobase, n = 1
Ru
Chem. Eur. J. 2601 26132007 13 -, , 9 ,
22
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
A Ditertiary-Phosphane-Bridged Heteronuclear ClusterOs
Synthesis and Reactivity with Alkynes
Y.L.K. TAN, W.K. LEONG
CM
Ru3(CO)12 + 3 C2H4
Ru(CO)4(C2H4) + dppm
Ru(CO)4(κ1-dppm) + Os3(µ-H)2(CO)10
3 Ru(CO)4(C2H4)hν
Ru(CO)4(κ1-dppm) + C2H4
RuOs3(µ-H)2(CO)9(µ-CO)2(µ-dppm) + 3 CO
Ru
Eur. J. Inorg. Chem. 1585 15982007 -, , 11 ,
Activation of Hydrogen by an Unsaturated Pt-Os Cluster complexOs
ADAMS R.D.; CAPTAIN B.; ZHU L.
GN
PBu3
Os
Pt
Os
PBu3
Os
Pt
PBu3
Pt
Os
PBu3
PtH
Os OsH
PBu3
PBu3
PtH
Os
H
Os
H
Pt
Os
H
0°C+ H2
0°C+ H2
25°C- H2
25°C- H2
Preparation of unsaturated pentanuclear platinium-osmium cluster complex that can reversibly absorb large amounts of hydrogen
Pt
J. Am. Chem. Soc. 2454 24552007 129 -, , 9 ,
Design of Cytotoxic Anticancer Os(II) Arene ComplexesOs
PEACOCK A.F.A.; PARSON S.; SADLER P.J.
GN
R
N
OOs
X
Study of the hydrolitic and aqueous solution chemistry of half-sandwich Os(II) arene complexes that can be tuned with N,O-chelating ligands to achieve cancer cell cytotoxicity comparable to carboplatin
J. Am. Chem. Soc. 3348 33572007 129 -, , 11 ,
Osmium Catalyzed Asymmetric DihydroxylationsOs
Study on the hydrolysis step of osmium (mono)glycolates of styrenes
M.H. JUNTTILA, O.E.O. HORMI
CM
O
O
R
OsO
OL
(VI)
J. Org. Chem. 2956 29612007 72 -, , 8 ,
23
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
A Recyclable Osmate-Exchanged Chloroapatite CatalystOs
for Catalytic Asymmetric Dihydroxylation of Olefins
S.K. DEHURY, V.S. HARIHARAKRISHNAN
CM
RR'
RR'
OH
OH
yield: 71-96%ee: 90-97%
CAP-OsO4(DHQD)2PHAL
t-BuOH-H2ONMO, RT
Tetrahedron Lett. 2493 24962007 48 -, , 14 ,
Bis(indolyl)maleimide PyridinophanesCo
Bis(indolyl)maleimide pyridinophanes are potent selective inhibitors of glycogen synthase kinase-3.
ZHANG, H.-C.; BONAGA, L. V. R.; YE, H.; DERIAN, C. K.; DAMIANO, B. P.; MARYANOFF, B. E.
PL
N
HN
O O
N
N
HN
O O
N
N
NRR'
R = R' = Me or R, R' = (CH2)4
+ isomerRR'N-CN
CpCo(CO)21,4-dioxane
115-11°C, 24 h
9-12% yield
Bioorg. Med. Chem. Lett. 2863 28682007 17 -, , 10 ,
Cobalt Catalyzed Formation of Methylenecyclopentanol from Allene and EnoneCo
CHANG, H.-T.; JAYANTH, T. T. ; CHENG, C.-H.
PJF
R1
R2
OR
2
HR
1
OHCoI2(dppe)
Zn, ZnI2
CH3CN, H2O
+
R1 = Alkyl, ArR2 = Alkyl
60-90%
J. Am. Chem. Soc. 4166 41672007 129 -, , 14 ,
Cobalt Carbometallation of Norbornen with EthyleneCo
BIANCHINI, C.; GIAMBASTIANI, G.; MELI, A.; TOTI, A.
PJF
N
NCo
Cl Cl
Co catalyst
up to 97%rd > 99%
Catalsyt
methylaluminoxaneethylene
Organometallics 1303 13052007 26 -, , 6 ,
24
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Oligomerization of Ethylene by Cobalt(II) 6-(Thienyl)-2-(imino)pyridine CatalysisCo
EPR studies demonstrate a spin state changeover upon activation of the catalyst by MAO
BIANCHINI, C.; GATTESCHI, D.; GIAMBASTIANI, G.; RIOS, I.G.; IENCO, A.; LASCHI, F.; MEALLI, C.; MELI, A.;SORACE, L.; TOTI, A.; VIZZA, F.
AN
NBrO
NH2
MeOH reflHCOOH (cat.)
NBrN
S
SnMe3
Pd(PPh3)4
NNS
NNS Co
Cl Cl
CoCl2THF
Organometallics 726 7392007 26 -, , 3 ,
Kinetic Studies on the Cobalt-Catalyzed Norbornadiene Intermolecular PK ReactionCo
CABOT, R.; LLEDO, A.; REVES, M.; RIERA, A.; VERDAGUER, X.
AN
SiMeMe
Me+
Co2(CO)8 cat.
∆, CO
H
H
O
TMS
Organometallics 1134 11422007 26 -, , 5 ,
Synthesis of 4-(Cyclopropylmethylene)cyclopentenonesCo
6 examples, yields: 43-59%; Pauson-Khand reactions with allenes.
AHMAR, M.; KNOKE, M.; DE MEIJERE, A.; CAZES, B.
GJ
Et
Et
Co2(CO)
6
O
Et
Et
+NMO, 0-20°C
CH2Cl2, THF
54%(Z/E 5:95)
Synthesis 442 4462007 -, , 3 ,
Continuous Enantioselective Kinetic Resolution of Terminal EpoxidesCo
Jacobsen’s cobalt-salen complex covalently linked on polymer carriers; continuous-flow reaction.
SOLODENKO, W.; JAS, G.; KUNZ, U.; KIRSCHNING, A.
GJ
OH O O
OH
(CF3)3COH linkerCo
t-BuO
t-B u
N
O
t-Bu
N
OAc
+
catalyst(2.8 mol%)
(0.2 equiv)(5 equiv))
THF, rt
93% (ee 95.5%)
catalyst
Synthesis 583 5892007 -, , 4 ,
25
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Regioselective Ring-Opening in Hexopyranosides Co
TANI, S.; SAVARDI, S. KOJIMA, M.; AKAI, S.; SATO, K.-I.
GP
O
O
O X
OROR'
Ph
OH
O
O X
OROR'
Ph
CoCl2 (3 eq.)
BH3.THF (3 eq.)THF, r.t., 10 min.
6 examples85%-quant.
Tetrahedron Lett. 3103 31042007 48 -, , 17 ,
Catalysed Substitutive Arylation of cis-Allylic Diols with ArylboroxinesRh
Asymmetric version (41 - 87 % ee) developed with BINAP or Carreira’s chiral diene.
MIURA, T.; TAKAHASHI, Y.; MURAKAMI, M.
AF
OHHO + (ArylBO)3
[Rh(OH)(cod)]2(2.5 mol %)
dioxaner. t., 12 h
HO
Ar(3 equiv.)
22 - 81 %
Ar: 4-Me-C6H4, 4-F-C6H4, 3-MeO-C6H4, 1-naphtyl, PhCHCHCH2
Chem. Commun. 595 5972007 -, , 5 ,
(1-Phosphanylferrocen-1’- and -2-yl)methyl-Linked Diamino Ruthenium CarbeneRh
LABANDE, A.; DARAN, J-C.; MANOURY, E.; POLI, R.
DL
PPh2
NN
R
1) t-BuOK, [Rh(COD)Cl]2THF
2) NaBF4, DCM/H2O, rtor AgBF4, DCM, rt.
Ph2P
N N R
Rh
+
75-81% yield
NN
R
1) t-BuOK, [Rh(COD)Cl]2THF
2) NaBF4, DCM/H2O, rtor AgBF4, DCM, rt.
+PPh2
NN
RPh2PRh
77% yieldR: Me, 2,4,6-Me3C6H2
FeBF4
- Fe
BF4-
Fe
BF4-
BF4-
Fe
Eur. J. Inorg. Chem. 1205 12092007 -, , 9 ,
Rhodium(I) Complexes Containing ββββ-Amino Alcohol and 1,2-Diamine LigandsRh
DAHLENBURG, L.; TREFFERT, H.; FARR, C.; HEINEMANN, F. W.; ZAHL, A.
DL
[(η4-C8H12)2Rh2(µ-Cl)2]
NH
RhCl
+
H2NOH
iPrOH
iPr KOH RhNH
O
iPr
Eur. J. Inorg. Chem. 1738 17512007 -, , 12 ,
26
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Rh-Catalysed Asymetric HydrogenationRh
22 exemples are described.
DARCEL, C.; MOULIN, D.; HENRY, J-C.; LAGRELETTE, M.; RICHARD, P.; HARVEY, P. D.; JUGÉ, S.
DL
Ph
MeO2C NHCOMe H2, solvent
[Rh(COD)L]+BF4-
Ph
MeO2C NHCOMeH
ONMe
PhMe
P R3R2
PPhR1
L:
R1: Ph, o-An, o-MEMPh, 1-Np, Fc, 2-Np, o-biPh, t-Bu, Me, C6H11
solvent: C6H6, DCM, MeOH, i-PrOH, EtOH
R2, R3: OPh, Ph, o-An
60-99% yield1-99% ee
Eur. J. Org. Chem. 2078 20902007 -, , 13 ,
Sequential Silylcarbocyclization / Cross-Coupling of EnynesRh
DENMARK, S. E., LIU, J. H.
CJM
XR
YX
Y
R
SiMe2BnX
Y
R
ArR= H, MeX= CE2, NBn, OY= H, CO2Et
HSiMe2BnRh4(CO)12
CO (1 Atm)hexane
TBAF 2 Eq.Ar-IPd2dba3 2.5%
THF, rt
PdSi
J. Am. Chem. Soc. 3737 37442007 129 -, , 12 ,
Synthesis of Functionalized Arenes Through Rh(I)-Catalyzed [2+2+2]CycloadditionRh
CLAYDEN J.; WESLEY J. M.
AE
R1
X
R1
R2
R1
R1
R2X10 mol% Rh(cod)2BF410 mol% rac-BINAP
yield : 56 to 93%X = C(CO2Me)2, O, NTsR1 = Me, Et, PhR2 = H, Me, OMe
Org. Biomol. Chem. 1028 10302007 5 -, , 7 ,
Base-Promoted Selective Activation of Benzylic C-H Bonds of Toluenes by Rhodium(III)Porphyrins
Rh
CHAN, K.S.; CHIU, P.F.; CHOI, K.S.
AN
Rh(ttp)Cl +
FG
CH3
10 equiv. base
120°C, N 2
FG
Rh(ttp)ttp = tetrakis-(4-tolylporphyrin)
FG = OMe, 92% tBu, 98% Me, 90% 3,5-Me2, 45% H, 90% F, 97% CN, 83% NO2, 98%
Organometallics 1117 11192007 26 -, , 5 ,
27
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Reactivity of Rhodium(I) Iminophosphine Carbonyl Complexes with Methyl IodideRh
BEST, J.; WILSON, J.M.; ADAMS, H.; GONSALVI, L.; PERUZZINI, M.; HAYNES, A.
AN
Rh
I
P
N
CO
Rh
I
P
N
CO
Rh
I
P
N
Ik1 MeI
k-1
k2
k-2
Me
I
COMe
Ph2P N
R1
R3R5
R4R2
PN=
Organometallics 1960 19652007 26 -, , 8 ,
Activation of Aldehydic Carbon-Hydrogen Bonds under Aerobic Conditions by MaskedRhodium(III) Porphyrin Cation
Rh
high yields of Rh(ttp)COR under anaerobic or aerobic conditions have been reached
CHAN, K.S.; LAU, C.M.; YEUNG, S.K.; LAI, T.H.
AN
Rh(ttp)CH2CH2OH
FGOHC
THF, 50°CFG
(ttp)Rh
O
ttp = tetrakis-(4-tolylporphyrin)
Organometallics 1981 19852007 26 -, , 8 ,
Phenols from CyclobutenonesRh
A mechanism via ketene formation is proposed.
KONDO, T.; NIIMI, M.; NOMURA, M.; WADA, K.; MITSUDO, T.-A.
GP
R
R
OR'
O
R
R
OH
R'
O
+
RhCl(C2H4)2 (5%)
P(c-C6H11)3, 10%toluene, 130°C, 12h
5 examples40-65%
Tetrahedron Lett. 2837 28392007 48 -, , 16 ,
Enantioselective [2+2+2] Cycloaddition of Diynes and Monoalkynes Ir
Several examples are reported on the preparation of axial chiral compounds.
SHIBATA, T.; ARAI, Y.; TAKAMI, K.; TSUCHIKAMA, K.; FUJIMOTO, T.; TAKEBAYASHI, S.; TAKAGI, K.
AF
NapZ
Nap
OH
OHNap = 1-naphtylZ = O, NTs, CH2
ZOHOH
43 - 98 %
99% ee
[Ir(cod)Cl]2 (10 mol %)(S,S)-MeDUPHOS (20 mol %)
xylener. t. or reflux
2 - 72 h
+
Adv. Synth. Catal. 2475 24832007 348 -, , 16-1
,
28
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
2,4-Dimethylpentane Dyads and 2,4,6-Trimethylheptane Triads PreparationIr
ZHOU, J.; BURGESS, K.
AF
TBDPSO
OH
TBDPSO OH
syn/antiD-1 12:1L-1 1:6
"Ir"(1 mol %)
+ H250 atm CH2Cl2
25 °C, 4 h O N
N
NIr
PriPr
i(cod)
+BArF-L-1:
Angew. Chem. Int. Ed. 1129 11312007 46 -, , 7 ,
Ir(III) Tolylterpyridine Complexes: Synthesis, Characterization and DFT studiesIr
Physical properties are provided
YOSHIKAWA, N.; YAMABE, S.; KANEHISA, N.; KAI, Y.; TAKASHIMA, H.; TSUKAHARA, K.
DL
(NH4)3[IrCl6]+
tterpy
1) ethylene glycol
mW, 3min2) L, 12min
3) KPF6 aq.sat.
IrN N
NN
N
Clif L=dmbpy
63% yieldlight yellow
L: Phen, dpphen, bpy,
Eur. J. Inorg. Chem. 1911 19192007 -, , 12 ,
Catalyzed Coupling of Alkenes and Aldehydes Ni
HO, C.-H.; JAMISON, T.F.
AF
R1+ R2-CHO R
1R2
OSiEt3
Ni(cod)2 (20 mol %)I (20 mol %)
P(OPh)3 (20 mol %)
Et3SiOTf, NEt3toluene up to 99%
N N
iPr
iPr
Pr
Pr
i
i
I:
Angew. Chem. Int. Ed. 782 7852007 46 -, , 5 ,
Carbocyanation of AlkynesNi
The Lewis acid has a dramatic effect on the reaction outcome.
NAKAO, Y.; YADA, A.; EBATA, S.; HIYAMA, T.
GP
R'
Ar
R R'
CNArCN + R
Ni(cod)2 (1%)-PMe3 (4%)AlMe3 (4%)
toluene, 80°C
17 examples78-94%
AlB
J. Am. Chem. Soc. 2428 24292007 129 -, , 9 ,
29
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
The Mechanism of Polymerization of Butadiene by “Ligand-Free” Ni(II) ComplexesNi
O’CONNOR, A. R.; WHITE, P. S.; BROOKHART, M.
MVI
CH3
Ni
F3C CF3
B(ArF)3 CH3
Ni
CD2Cl2
CH3
Ni
-63°C
-110°C
J. Am. Chem. Soc. 4142 41432007 129 -, , 14 ,
Role of Styrene in Nickel-Catalyzed Anhydride Cross-CouplingNi
Effect of styrene was demonstrated in both system
JOHNSON, J. B.; BERCOT, E. A.; ROWLEY, J. M.; COATES, G. W.; ROVIS, T.
MVI
O
O
O
H
H
Ni(COD)2
Et2Zn
Et
O
OH
O
H
H
O
O
O
Ni(COD)2
Et2ZnO
Et
O
OH
PPh2
N
Obipy
4-F-styreneiPrPHOXstyrene
iPrPHOX
Rate LimitingReductive Elimination
Rate LimitingOxidative Addition
J. Am. Chem. Soc. 2718 27252007 129 -, , 9 ,
Ni(0)-Promoted HydroxycarboxylationNi
AOKI, M.; IZUMI, S.; KANEKO, M.; UKAI, K.; TAKAYA, J.; IWASAWA, N.
CC
CR
R R
R
1
2
3
4R
R
R
ROH
COOMe
1
2
3
4
RR
R
RHOCOOMe1
2
3 4
i) CO2 (1 atm), dtbpy (1.1 eq), Ni(cod)2 (1 eq), THF, 0°C, 2hii) HCl/MeOH, -78°C then O 2, -78°C, 2h
iii) Me2S, 0°Civ) TMSCHN2, MeOH, 0°C
+
8 ExamplesYields = 44 - 82%
R1, 2, 3, 4 = H, alkyl, cycloalkyl, Ph, CH2CH2Ph
Org. Lett. 1251 12532007 9 -, , 7 ,
Pd-Catalyzed Hydrogenolysis of Benzylic Nitro GroupPd
This represent new opportunities in asymmetric synthesis
FESSARD, T.C.; MOTOYOSHI, H.; CARREIRA, E.M.
CY
Ar
NO2
*Ar *
Pd(OH)2/C (5-10 mol%), EtOH, H2 (1 bar), 70 °C
many examples, 50-95%
Angew. Chem. Int. Ed. 2078 20812007 46 -, , 12 ,
30
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Borosalicylic Acid: an Advantageous Promoter for the Methoxycarbonylation of Ethylene Pd
FERREIRA, A.C.; CROUS, R.; BENNIE, L.; MEIJ, A.M.M.; BLANN, K.; BEZUIDENHOUDT, B.C.B.; YOUNG, D.A.; GREEN,M.J.; ROODT, A.
CY
+ CO + MeOH
Pd(OAc)2, PPh3,B(OH)3, salicylic acid
O
OMe
Angew. Chem. Int. Ed. 2273 22752007 46 -, , 13 ,
Three-Component Cross-Coupling of Aryl Halides, Alkynes and ArynesPd
Various polycyclic aromatic compounds are prepared
LIU, Z.; LAROCK, R.C.
CY
R1
I
R2 R3 R4 R4
R2
R3
R1
Pd(dba)2 (5 mol%), CsF (3 equiv),TlOAc (1.2 equiv),1:1 MeCN:toluene, 90 °C, 8 h
++56-91%
Angew. Chem. Int. Ed. 2535 25382007 46 -, , 14 ,
Substituted 2-Pyridylmethyl from Aromatic Halides and 2-(2-Pyridyl)-ethanolPd
NIWA, T.; YORIMITSU, H.; OSHIMA, K.
CY
Cl
ClCl
N
N
N
Pd(OCOCF3)2 (15 mol%)PCy3 (30 mol%)
Cs2CO3 (3.6 equiv)xylene, reflux, 10 hNOH
iPriPr+ 3
81%
Angew. Chem. Int. Ed. 2643 26452007 46 -, , 15 ,
Alcohols Oxidation Catalyzed by Palladium in Carbon WallsPd
LU, A.-H; LI, W.-C.; HOU, Z.; SCHÜTH, F.
BJL
RCH2OHPd/OMC
OMC : ordered mesoporous carbon
80-100°C
RCHO RCH2OH : benzyl alcohol 1-phenylethanol, cinnamyl alcohol
selectivity >99%
Chem. Commun. 1038 10402007 -, , 10 ,
31
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Synthesis of Substituted Benzene Fused with Carbocycles and HeterocyclesPd
SWAMY, N. K.; TATINI, L. K.; BABU, J. M.; ANNAMALAI, P.; PAL, M.
BJL
OI PdCl2(PPh3)2 cat
80°C+ RH
O
R
R
50-80%
Chem. Commun. 1035 10372007 -, , 10 ,
Synthesis of the First Pyrazolin-4-ylidene Complexes of Palladium(II)Pd
HAN, Y.; HUYNH, H. V.
BJL
R1 R1
OO
1. R2NHNH22. KI/I23. EtI
NN
I+
I-R2
1. Pd2(dba)3, PPh32. AgO2CCF3
NN
Pd+
R2O2CCF3
PPh3
O2CCF3
Chem. Commun. 1089 10912007 -, , 10 ,
Synthesis and Reactivity with Amines of Alkylpalladium N-Heterocyclic CarbenePd
The factors that might be barriers to the Pd-catalyzed alkyl-amination is discussed
ESPOSITO, O.; LEWIS, A. K. K.; HITCHCOCK, P. B.; CADDICK, S.; CLOKE, F. G. N.
BJL
Pd
N
N
t-Bu
t-Bu Pd
N
N
t-Bu
t-BuCl
Cl
RR'NHPd NHRR'ClN
N
t-Bu
t-Bu
RR'NH : morpholine hexylamine
Chem. Commun. 1157 11592007 -, , 11 ,
Magnetic Pd Nanoparticles for C-C Bond FormationPd
Suzuki and Sonogashira coupling are also presented
YOON, H.; KO, S.; JANG, J.
BJL
Pd nano (cat)3.8 nm
2 recycling
I
+
97%
Chem. Commun. 1468 14702007 -, , 14 ,
32
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
9-Fluorenylphosphines for Pd Cross-Coupling ReactionsPd
FLECKENSTEIN, C. A.; PLENIO, H.
MF
ClR R
1 % [Pd] / 2 % L0.75 % CuI
DMSO, 100-120 °C
PR2H+
BF4-
L : 9-Fluorenylphosphines
Chem. Eur. J. 2701 27162007 13 -, , 9 ,
Sugar-Based Ligand for Asymmetric Pd-Catalyzed Heck ReactionsPd
MATA, Y.; PAMIES, O.; DIÉGUEZ, M.
MF
O
O
OTf
O
O
[Pd] / L
MW / 70 °C
high ee, high conversion
OO
O
N O
R
OP
O O
Ph
L : Phosphite–Oxazoline
Chem. Eur. J. 3296 33042007 13 -, , 12 ,
N-Type Conjugated Materials Through Heck ReactionPd
Promising candidates for use as organic solar cells
SHIN, R. Y. C.; KIETZKE, T.; SUDHAKAR, S.; DODABALAPUR, A.; CHEN, Z.-K.; SELLINGER, A.
MVI
N N
CNNC
RAr BrBr
N
NNC
NC
RAr
N
N CN
CN
R+
2% [Pd(P(t-Bu)3)2]
2.5 equiv. Cy2NMe
DMF, 80°C
Chem. Mater. 1892 18942007 19 -, , 8 ,
Coordination Constants of Differents Ligands based on a Pd Pincer ComplexPd
MINAKAWA, M.; TAKENAKA, K.; UOZUMI, Y.
MF
Pd
Cl
NNPh
HaHa
Ph
HaHa
Hb Hb
Pd
Cl
NNPh
HaHa
Ph
HaHaHb HbL L
L
L : P-coordinating ligands, As-coordinating AsPh3, N-coordinating pyridine
Eur. J. Inorg. Chem. 1629 16312007 -, , 12 ,
33
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Ionic Liquid Effect in Buchwald-Hartwig Amination R eactionPd
MCNULTY, J.; CHEEKOORI, S.; BENDER, T. P.; COGGAN, J. A.
BJL
Br + NHPd(0) cat / PR3 cat
t-BuONa, IL, ∆N IL : trialkylphosphonium salt
72-75 %
Eur. J. Org. Chem. 1423 14282007 -, , 9 ,
Ligand-free Suzuki ReactionPd
DENG, C.-L.; GUO, S.-M.; XIE, Y.-X.; LI, J.-H.
BJL
XR1
B(OH)2R2
+Pd(OAc)2 cat
MeONa, rt R1 R2
9-99%
Eur. J. Org. Chem. 1457 14622007 -, , 9 ,
Stereoselective Oxazine FormationPd
JOO, J.-E.; LEE, K.-Y.; PHAM, V.-T.; HAM, W.-H.
BJL
R
NHBz
OTBS
ClPd(0) cat
Base, n-Bu4NIN O
Ph
R
OTBS
59-89%syn/anti 14/1-1/16
Eur. J. Org. Chem. 1586 15932007 -, , 10 ,
Buchwald-Hartwig Coupling of Aminothiophenes with HalopyridinesPd
BEGOUIN, A.; HESSE, S.; QUEIROZ, M.-J. R. P.; KIRSCH, G.
BJL
SNH2
R2
R1
CO2Me
+NX R Cs2CO3, ∆
X = I, Br, ClR = H, X
SNH
R2
R1
CO2Me
N
R13-73%
Eur. J. Org. Chem. 1678 16822007 -, , 10 ,
34
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Bromo-Cyano-Substituted Azulene Building Block for Acetylenic ScaffoldingPd
PETERSEN, M. Å.; KILSÅ, K.; KADZIOLA, A.; NIELSEN, M. B.
BJL
NC CNPh Ph
NC
Br
Pd(II) catt-Bu3P, CuI
SiMe3
NHi-Pr2
Ph
NC
SiMe3
1. Base2. Cu(I) cat
79% 27%
PhNC
2
Cu
Eur. J. Org. Chem. 1415 14182007 -, , 9 ,
Carbonylative Suzuki-Miyaura for the Synthesis of Unsymmetrical DienonesPd
BARTALI, L.; GUARNA, A.; LARINI, P.; OCCHIATO, E. G.
BJL
X OTf B(OH)2R1
R2+
Pd(OAc)2 5%, PPh3 10%
CO (1atm), base, THF XO
R1
R2
31-83%
B
Eur. J. Org. Chem. 2152 21632007 -, , 13 ,
Imidazolium-Based Ionic Liquid for Heck ReactionsPd
The catalyst was reused six times
IRANPOOR, N.; FIROUZABADI, H.; AZADI, R.
BJL
XR1
+ R2PdCl2 (cat), IL
NEt3, ∆
R1 R2
IL:NN
PF6
OPPh2
60-97%X = Cl, Br, I
Eur. J. Org. Chem. 2197 22012007 -, , 13 ,
Enantioselective Cyclization of Silyloxy 1,6-EnynesPd
CORKEY, B. K.; TOSTE, F. D.
CJM
I
Me
OTBS ((R)-DTBM-Segphos)Pd(OTf)2 10%
96% yield, 95% ee
OI
Me
J. Am. Chem. Soc. 2764 27652007 129 -, , 10 ,
35
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Methylation and Arylation of C-H Bonds in Carboxyli c AcidsPd
Ortho methylation and arylation of benzoic acids are also described
GIRI, R.; MAUGEL, N.; LI, J.; WANG, D.; BREAZZANO,S. P.; SAUNDERS, L. B.; YU, J.
CJM
R COOHMe Me
+ Ar BO
OPd(OAc)2 10%Benzoquinone
Ag2CO3, K2HPO4t-BuOH, 100 °C
R COOHMe
Ar
J. Am. Chem. Soc. 3510 35112007 129 -, , 12 ,
Enantioselective Desymetrization Using a C-C Bond CleavagePd
OHMURA, T.; TANIGUCHI, H.; KONDO, Y.; SUGINOME, M.
CJM
B(pin)Ph2MeSi +
R
R
R
R
SiMePh2
B(pin)
5 examples50-95% yield81-91% ee
Pd(dba)2 2%L* 2.4%
toluene, 50 °C
PAr3L*=
SiB
J. Am. Chem. Soc. 3518 35192007 129 -, , 12 ,
Dialkoxylation of 2-Propenyl PhenolsPd
ZHANG, Y.; SIGMAN, M. S.
CJM
R2
OHR1
Pd(MeCN)2Cl2 10%Quinox 12%
O2, ROH, 3Årt
R2
OHR1
OR
ORR2
OPdCl
ORR1
H
J. Am. Chem. Soc. 3076 30772007 129 -, , 11 ,
Total Synthesis of Marcfortine B via a TMM CycloadditionPd
TROST, B. M.; CRAMER, N.; BERNSMANN, H.
CJM
NBoc
OMeOMe
O +
TMS
TMS
OCO2Me
OMeOMeN
Boc
O
HO2CPd(OAc)2 5%P(O-i-Pr)3 35%
toluene, reflux
93%
J. Am. Chem. Soc. 3086 30872007 129 -, , 11 ,
36
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Carbocyclic Carbene LigandsPd
Low (8.10-5 mol %) catalyst loadings are described for Heck reactions
YAO, Q.; ZABAWA, M.; WOO, J.; ZHENG, C.
CJM
R R
PdNO
OAc
J. Am. Chem. Soc. 3088 30892007 129 -, , 11 ,
Monophosphine-Based Catalysts for Suzuki-Miyaura Reactions on HeteroaromaticsPd
Efficient ligands for the Suzuki-coupling of boronic derivatives with heteroaryl-halides
BILLINGSLEY, K.; BUCHWALD, S. L.
CJM
PCy2MeO OMe
PCy2i-Pr
i-Pr
i-Pr
J. Am. Chem. Soc. 3358 33662007 129 -, , 11 ,
Kumada-Corriu Cross-Coupling Reactions with Knochel-type Grignard ReagentsPd
MARTIN, R.; BUCHWALD, S. L.
CJM
PCy2Me2NR1
I+ R2
MgX
R1R2
Pd(dba)2 2%L 3%
Toluene / THF-20 °C
L=
21 examples
Mg
J. Am. Chem. Soc. 3844 38452007 129 -, , 13 ,
Total Synthesis of 2’-O-Methylmyxalamide DPd
COLEMAN, R. S.; LU, X.; MODOLO, I.
CJM
HO NH
OOMe
Stille-Coupling Suzuki-CouplingBSn
J. Am. Chem. Soc. 3826 38272007 129 -, , 13 ,
37
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Polymerization of CO/ethene: DFT studiesPd
Steric bulk and wide bite angles favors ester formation over polymerization
ZUIDEMA, E.; BO, C.; VAN LEEUWEN, P. W. N. M.
CJM
PPd
P
OC H
CO /
O
OVs.
O
nmethanol
J. Am. Chem. Soc. 3989 40002007 129 -, , 13 ,
Allylation of Aldehydes with Vinyl EpoxidePd
KIMURA, M.; MUKAI, R.; TAMAKI, T.; HORINO, Y.; TAMARU, Y.
CJM
R1 R2
OO
R1 R2
O
OH
Pd(acac)2nBu3PEt3B
R1R2
HO
THF 50 °CPd(Ph3P)4DMSO, rt
J. Am. Chem. Soc. 4122 41232007 129 -, , 14 ,
Decarboxylative Coupling of Heteroaromatic AlkanesPd
WAETZIG, S. R.; TUNGE, J. A.
CJM
HetAr
R1O
O
R2Pd(Ph3P)4 5%
toluene, 100 °C
HetAr
R1
R2R3 R316 examples30-95% yields
J. Am. Chem. Soc. 4138 41392007 129 -, , 14 ,
Insertion of Oxygen into a Palladium-Hydride BondPd
The two pathways are isoenergetic
POPP, B. V.; STAHL, S. S.
CJM
AcO PdII
NHC
NHC
HO2
AcO PdII
NHC
NHC
H OO
vs. PdII
O
ONHC
NHCAcO PdII
NHC
NHC
OOH
J. Am. Chem. Soc. 4410 44222007 129 -, , 14 ,
38
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Allylation of Aryl Halides via a Retro-AllylationPd
IWASAKI, M.; HAYASHI, S.; HIRANO, K.; YORIMITSU, H.; OSHIMA, K.
CJM
R2
OH
R5R1
R6R7
R3 R4
+ Ar-X
Pd(OAc)2 / PCy3Cs2CO3
toluene, reflux
R6ArR7
R3
R4R5
J. Am. Chem. Soc. 4463 44692007 129 -, , 14 ,
Bicycles via a Cyclization-Oxidation SequencePd
TONG, X.; BELLER, M.; TSE, M. K.
CJM
R
O X
Pd(OAc)2 10%
2 Eq. PhI(OAc)2AcOH X
OO
R8 examplesR= O, NTs51-83%
J. Am. Chem. Soc. 4906 49072007 129 -, , 16 ,
Asymmetric Allylic Trichloroacetamidate Rearrangement.Pd
A model (DFT studies) for enantioinduction is discussed
WATSON, M. P.; OVERMAN, L. E.; BERGMAN, R. G.
CJM
O NH
CCl3
R R
NH
CCl3
OPdL*
J. Am. Chem. Soc. 5031 50442007 129 -, , 16 ,
Intramolecular C-H Activation via an Aryl to Imido yl Palladium MigrationPd
ZHAO, J.; YUE, D.; CAMPO, M. A.; LAROCK, R. C.
CJM
N
I
ZR1 R2
Z
O
R1 R2
Pd(OAc)2 5%dppm 5%CsPiv 2 Eq.
DMF, 100 °C
J. Am. Chem. Soc. 5288 52952007 129 -, , 16 ,
39
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Total Synthesis of (-)-TerpestacinPd
TROST, B. M.; DONG, G.;VANCE, J. A.
CJM
O
OHO+
Pd2dba3 CHCl3 1%Trost L* 2.6%Bu4NCl 50%
DCM95% yield, 96% ee
O
OOH
O
HO
HOOH
J. Am. Chem. Soc. 4540 45412007 129 -, , 15 ,
Decarboxylative Cross-Coupling ReactionsPd
GOOSSEN, L. J.; RODRIGUEZ, N.; MELZER, B.; LINDER, C.; DENG, G.; LEVY, L. M.
CJM
Ar OH
O
+
X
R
Ar
R + CO2
Pd(acac)2 2%P(i-Pr)Ph2 6%CuCO3, KFNMP, 120 °C
Pd(acac)2 1%CuI 3%Phenanthroline 5%K2CO3NMP,160 °C
or
Cu
J. Am. Chem. Soc. 4824 48332007 129 -, , 15 ,
Palladium-Catalyzed Formal [4+2] Cycloaddtion of o-Xylylenes with OlefinsPd
KUWANO, R.; SHIGE, T.
VM
SiMe3OCO2Me EWG
R
Pd(η3-C3H5)Cp (3 mol%)dppe (3.3 mol%)
DMSO, 120°C
R
EWG
47-92% Yield
Si
J. Am. Chem. Soc. 3802 38032007 129 -, , 13 ,
Synthesis of Alkynylpyrimidine Amide DerivativesPd
~ 20 exemples; tested as inhibitors of Tie-2 Kinase.
CEE, V.J.; ALBRECHT, B.K.; GEUNS-MEYER, S.; HUGHES, P.; BELLON, S.; BREADY, J.; CAENEPEEL, S.; CHAFFEE,S.C.; COXON, A.;EMERY, M.; FRETLAND, J.; GALLANT, P.; GU, Y.; HODOUS, B.L.; HOFFMAN, D.; JOHNSON, R.E.;
GJ
N
NNH2
O
NH
I
CF3 N
N
NH2
O
NH
CF3
Pd(PPh3)2Cl
2
+
2 equiv
(5 mol%)
CuI (5 mol%)
MeCN, Et3N, 80°C
69%
Cu
J. Med. Chem. 627 6402007 50 -, , 4 ,
40
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Pd-Catalyzed Synthesis of N-aryl-3-arylmethylisoxazolidinesPd
PENG, J.; LIN, W.; YUAN, S.; CHEN Y.
MV
ONH2
R
1 mol% Pd2dba32 mol% Xantphos
2.4 equiv. NaOt-Butoluene, 90°C, 3h
42-82%R = Ar, i-Pr
+ Ar-Br ONAr
R
Ar
Na
J. Org. Chem. 3145 31482007 72 -, , 8 ,
Heck Arylations of Allyl Alcohols in Ionic LiquidsPd
CALO, V.; NACCI, A.; MONOPOLI, A.; FEROLA, V.
MV
1.2 mol% Pd(OAc)2
TBAB, NaHCO370-1300C, 60-92%
R'
OH
R + Ar-X
X = Br, I
R'
O
R
Ar+
R'
O
R
Ar
1.2 mol% Pd(OAc)2
TBAA
R'
OH
Ar
R+
R'
OH
Ar
R
70-1300C, 60-92%
Na
J. Org. Chem. 2596 26012007 72 -, , 7 ,
Pd-Catalyzed N-arylation of Heterocyclic DiaminesPd
CABELLO-SANCHEZ, N.; JEAN, L.; MADDALUNO, J.; LASNE, M.-C.; ROUDEN, J.
MV
NH
+ Ar-Br
NH2
n
m
Cond.
n = m = 168%
NPh
NH2
Cond.
n = 1, m = 262%N
H
HNO Cond. = Pd2dba2 (1 mol%), BINAP (1.5 mol%)
NaOt-Bu (1.4 equiv.)toluene, 110°C, 24h
Na
J. Org. Chem. 2030 20392007 72 -, , 6 ,
Pd-Catalyzed C-P Coupling Reactions Between Vinyltriflates and Phosphine-BoranesPd
JULIENNE, D.; LOHIER, J.-F.; DELACROIX, O.; GAUMONT, A.-C.
MV
OTf
R2
R1
R1
+ PH
BH3
R3R4
5.6 mol% dpppPdCl2
K2CO3, DMSO60°C, 75-90%
P
R2
R1
R1
R3
R4
BH3R1 = H, Ph, MeR2 = Me, t-Bu, HR3 = Me, Et, CyR4 = Ph, Me, Et, Cy
K
J. Org. Chem. 2247 22502007 72 -, , 6 ,
41
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Synthesis of 4-AminoquinolinesPd
MARGOLIS, B.J.; LONG, K.A.; LAIRD, D.L.T.; RUBLE, J.C.; PULLEY, S.R.
MV
4 mol% Pd(OAc)28 mol% DPEphos
dioxane, 85°C32-88%
+ Ar-BrR2HN NH2
R'N
NH
R'
R2HN
Y
XR = Me, EtR' = MeX = Cl, NO2Y = H, SMe, OMe, Br, CN, CO2Me, F
J. Org. Chem. 2232 22352007 72 -, , 6 ,
Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBNPd
LIRON, F.; FOSSE, C.; PERNOLET, A.; ROULLAND, E.
MV
R
2.5 mol% Pd2dba35 mol% Xantphos
THF, refluxKF-K3PO4 or CsF-Cs2CO3
58-88%R = Ar, cyclopropyl, alkylR' = Bn, pentyl, CH2OBn
Cl
Cl
+B R'
R
Cl
R'KCs
J. Org. Chem. 2220 22232007 72 -, , 6 ,
Pd/C Redox Reactions between Aliphatic Secondary Alcohols ad KetonesPd
ESAKI, H.; OHTAKI, R.; MAEGAWA, T.; MONGUCHI, Y.; SAJIKI, H.
MV
R
OH
R'
10% Pd/CH2
D2O, ∆R
O
R'
R, R' = alkyl
CuK
J. Org. Chem. 2143 21502007 72 -, , 6 ,
Palladacycle as Catalyst for Ring Opening of Oxabicyclic Alkenes.Pd
Palladacycle as highly efficient catalyst for oxabicyclic opening with organozinc halides is reported.
ZHANG, T-K.; YUAN, K.; HOU, X-L.
AM
O
R1R2
R2R1
R3 R1R2
R2R1
OH
toluene, 80 °C
ArCH2ZnBr, palladacycle A (0.05 mol%)R3
ArPd
N
BrPh3P
OA :
58-80% yields
J. Organomet. Chem. 1912 19192007 692 -, , 10 ,
42
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Synthesis of 4-Arylpiperidines from 1-Benzyl-4-piperidonePd
MORRILL, C.; MANI, N. S.
CS
N
R
BnN
Si
Bn
Me Me
Bn
H Cl
N
R
Bn
R-Br (1.5 equiv)TBAF (4 equiv)
PdBr2-2[2-(t-Bu2P)biphenyl](5 mol%)
THF, 50°C, 20h
R-I (1.5 equiv)TBAF (4 equiv)
Pd2dba3-CHCl3(2 mol%)
THF, rt or 50°C, 18-20h45-99%(R = aryl)64-99%
(R = aryl)
Org. Lett. 1505 15082007 9 -, , 8 ,
Aminomethylations via Cross-Coupling ReactionPd
2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl = XPhos
MOLANDER, G. A.; SANDROCK D. L.
CS
NR1
R2BF3K Br
R+ RNR1
R2
Pd(OAc)2 (3% mol)XPhos (6% mol)
Cs2CO3 (3 eq.)solvent, heat 10 examples, 66-83% yield
B
Org. Lett. 1597 16002007 9 -, , 8 ,
Enantioselective Synthesis of P-Stereogenic Benzophospholanes2007
Pd
BRUNKER, T. J.; ANDERSON, B. J.; BLANK, N. F.; GLUECK, D. S.; RHEINGOLD, A. L.
CS
I
PE
PhH P
PhE
cat. "Pd(Me-DuPhos)"
NaOSiMe3 (E = lone pair)or proton sponge (E = BH3)
59-70% ee
Org. Lett. 1109 11122007 9 -, , 6 ,
Arylation of Electron-Rich HeterocyclesPd
BuAd2P = butyldi-1-adamantylphosphine, No copper additives are needed.
CHIONG, H. A.; OLAFS DAUGULIS, O.
CS
N
N
NH
NOMe
Me
ArCl, Pd(OAc)2
NMP, K3PO4BuAd2P
N
N
NH
NOMe
MeMe
86%
Org. Lett. 1449 14512007 9 -, , 8 ,
43
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Pd-Catalyzed anti-Hydrothiolation of 1-AlkynylphosphinesPd
KONDOH, A.; YORIMITSU, H.; OSHIMA, K.
CS
PR22R1
R3SH
+R1 H
R3S PR22
cat. Pd(OAc)2
EtOH, 25°C, 1-4h
15 examples, 55-93% yield
Org. Lett. 1383 13852007 9 -, , 7 ,
Highly Efficient Ruthenium Catalysts forthe Formation of Tetrasubstituted
Pd
STEWART, I. C.; UNG, T.; PLETNEV, A. A.; BERLIN, J. M.; GRUBBS, R. H.; SCHRODI, Y.
CS
X
MeMe
n
X = C(CO2R)2, n = 1,2X =NTs, n = 1X= O, n = 1
X
n
MeMe
N N
Cl2Ru
Oi-Pr
0.1 M, C6H6, 60°C
> 95% conversion5- and 6-membered rings
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Cyanation of ArCl.Pd
Other similar ligands have been synthesised. Various bases and solvents tested. 13 examples.
CHENG, Y.-N.; DUAN, Z.; LI, T.; WU, Y.
MJ
ArCl
cat. (0.02 equiv.)
K4[Fe(CN)6].3H2O (0.22 eq.)
Na2CO3 (1 eq.)NMP, 140 °C, 18 h
ArCN81%
cat. :
Pd
N
Fe
ClPCy3
OEt
Fe
Synlett 543 5462007 -, , 4 ,
Three-Component Coupling.Pd
Various ligands and solvents tested. 8 examples.
YOSHIDA, M.; MURAO, T.; SUGIMOTO, K.; IHARA, M.
MJ
O
Ph
OH
OO
O
O
Ph
+
Pd2(dba)3.CHCl3 (0.05 eq.)
dppp (0.2 eq.)
dioxane, 50 °CMS 3Å
70%
+ CO2(1 atm.)
(1.2 eq.)
Synlett 575 5782007 -, , 4 ,
Coupling-Cyclization Procedure.Pd
Also with allylCl. 11 examples.
MA, S.; YU, F.; ZHAO, J.
MJ
C4H9
POH
OEtO
PdCl2(PhCN)2 (0.05 eq.)
DMF, 80 °C, 2 h
72% OP
C4H9
OEt
O
Br+
Synlett 583 5862007 -, , 4 ,
Sonogashira Reaction.Pd
Spectral properties (fluorescence).
REDDY, M. R.; SHIBATA, N.; YOSHIYAMA, H.; NAKAMURA, S.; TORU, T.
MJ
Zn
= phthalocyanine
I I
I I
Zn+ R
R = O
TolO
TolO
RR
R R75%
PdCl2(PPh3)2 (cat.)CuI (cat.)
NEt3, DMFrt, 72 h
Zn
Synlett 628 6322007 -, , 4 ,
45
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Carbonylative Cyclization.Pd
The products ratio depends on R and L. Chiral ligands have also been used (up to 95% ee).
KATO, K.; TERAGUCHI, R.; YAMAMURA, S.; MOCHIDA, T.; AKITA, H.; PEGANOVA, T. A.; VOLOGDIN, N. V.;GUSEV, O. V.
MJ
O
O
R
O
O
O
O
MeO
MeO
R
MeO2C
OMe
Pd(OCOCF3)2 (0.05 eq.)L (0.75 eq.)
p-benzoquinone (2 eq.)
CO (balloon)MeOH
+
R
up to 79%
Synlett 638 6422007 -, , 4 ,
Chiral Catalysts.Pd
Kinetic resolution of alcohols using these complexes.
NGUYEN, H. V.; MOTEVALLI, M.; RICHARDS, C. J.
MJ
N
Br
N PdCl2, P(t-Bu)3CsF, CuI
Fe
FeDMF, ∆
SnBu3
N
N
82%
+Co
N
N
14%
Othersynthesis:
Ph
PhPh
PhBr
Fe
FeCoZnSn
Synlett 725 7282007 -, , 5 ,
Cyclization.Pd
The reverse order of these 2 steps led to a lower yield.
DEUTSCH, C.; HOFFMANN-RÖDER, A.; DOMKE, A.; KRAUSE, N.
MJ
HO OTBS
H
Br
AuCl3 (0.01 eq.)
THF
72%
Br
O
OTBS
O
OTBS
Me3Si
SiMe3PdCl2(PPh3)2 (0.02 eq.)
CuI (0.04 eq.)
NEt392%
AuCu
Synlett 737 7402007 -, , 5 ,
Cross-Coupling.Pd
Lower yields with Pd(0) catalysts. 18 examples.
ENDO, M.; SAKURAI, T.; OJIMA, S.; KATAYAMA, T.; UNNO, M.; MATSUMOTO, H.; KOWASE, S.; SANO, H.; KOSUGI, M.;FUGAMI, K.
MJ
O
SiO
Si
OSi
Ar
Ar
ArAr
Ar
ArBr OMe+
Pd(OAc)2 (0.05 eq.)
KOH (10 eq.)
(ca. 0.2 eq.)
dioxane/H2O (1:1)reflux, 4 h
Ar = Ph: 87%
Ar OMe
Si
Synlett 749 7522007 -, , 5 ,
46
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
New Chelating Ligand. Heck Reaction.Pd
13 examples.
PATHAK, D. D.; MAHESWARAN, H.; PRASANTH, K. L.; KANTAM, M. L.
MJ
R
Ar
R
ArX +
R = Ar', COOMe, CNX = Br, I: 69-89%X = Cl: 20%
Cat. (0.05 eq.)n-Bu3N (1.2 eq.)
(1.2 eq.)DMF, 85-130 °C
Cat.:
N NH
O
PPd
O
P
Cl Cl
Synlett 757 7602007 -, , 5 ,
An Alternative Reagent fo Pd-Catalyzed Borylation of Aryl Halides Pd
MURATA, M.; ODA, T.; WATANABE, S.; MASUDA, Y.
PG
BH3.Me2S + OHHO
B
O
OH
CH2Cl20°C to rt
78 %
ArILigand
PdCl2(MeCN)2Et3N
PhCH380°C
B
O
O
Ar
9 examples72-93%
B
Synthesis 351 3542007 -, , 3 ,
High T.O.N. in Suzuki Cross-Coupling with a Phosphine Free Pd-CatalystPd
CUI, X.; QIN, T.; WAY, J.-R.; LIU, L.; GUO, Q.-X
PG
X
R
B(OH)2+
R
Pd(OCOCH2NMe2)K3PO4
50°C, air, 1hEtOH/H2O
X = Br, I 23 examples88-99%TON 104
R'
R'
B
Synthesis 393 3992007 -, , 3 ,
Pd-Catalyzed Synthesis of 5H-Imidazo[2,1-a]isoindolesPd
DE FIGUEIREDO, R. M.; THORET, S.; HUET, C.; DUBOIS, J.
PG
DMFµW, 15 min
N
NI
R'
R N
N
R
R
Pd(OAc)2 (10 mol%)P(o-Tolyl) (30 mol%)
AcOK 16 examples18-72%
Synthesis 529 5402007 -, , 4 ,
47
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Easy Access to γγγγ-Alkylidenebutenolide and Phthalide SkeletonsPd
DUCHENE, A.; THIBONNET, J.; PARRAIN, J.-L; ANSELMI, E.; ABARABRI, M.
PG
SnBu3
I
O
OSnBu3+
Pd(PPh3)4
DMFO
O
Bu3Sn
RXPdCl2(MeCN)2
O
O
R6 examples
65-75%10 examples
58-77%
Synthesis 597 6072007 -, , 4 ,
Microwave Assisted Heck Reaction in WaterPd
ZHU, M.; SONG, Y.; CAO, Y.
PG
WaterµW, 20 s
CO2H + Ar2I ClPdCl2 (1 mol%)
CO2HAr 9 examples
78-85 %
Synthesis 853 8562007 -, , 6 ,
Pd-Catalyzed Cross-Coupling Chiral BenzylsulfanyloxazolinesPd
LECONTE, N.; PELLEGATTI, L.; TATIBOUËT, A.; SUZENET, F.; ROLLIN, P.; GUILLAUMET, G.
PG
O
NSBn
RB(OH)2or
RSnBu3+
[Pd(0)]
O
NR
13 examples55-93%* *
BSn
Synthesis 857 8642007 -, , 6 ,
Palladium-Catalyzed Synthesis of 3,3-Disubstituted -2,3-Dihydrobenzofuran.Pd
SZLOSEK-PINAUD, M.; DIAZ, P.; MARTINEZ, J.; LAMATY, F
AM
OH
IBr
CO2MeO
I
+ CO2Me
O
CO2MeNu
base Pd cat./ Nu
one pot versionNu , Pd cat., base
20 examples
Tetrahedron 3340 33492007 63 -, , 16 ,
48
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Palladium-Catalyzed Amination and/or Nucleophylic Aromatic Substitution.Pd
Examination of the mecanism of the title intramolecular reaction is described.
LOONES, K. T. J.; MAES, B. U. W.; HERREBOUT, W. A.; DOMISSE, R. A.; LEMIERE, G. L. F.; VANDER VEKEN, B. J.
AM
X
NH
N
N
NPd - catalystor
base assistedSNAr
X = Br, Cl
Tetrahedron 3818 38252007 63 -, , 18 ,
Mecanistic Aspects in the Palladium-Catalyzed Reduction of Alkenes.Pd
BRUNEL, J. M.
AM
R4
R1 R2
R3 R4
R1 R2
R3yields varying from 25 to 98%
2 mol % Pd(OAc)24 mol % P(t-Bu)4
HCO2 (5 eq.)THF, reflux to r.t
Tetrahedron 3899 39062007 63 -, , 18 ,
Hydroxyl Group Deprotection Reactions with Pd(OH)2 / C.Pd
A convenient alternative to hydrogenolysis of benzyl ethers and acid hydrolysis of ketals is reported.
MURAL, C.; SHASHIDAR, M. S.; GOPINATH, C. S.
AM
O
O
R2R1
R-O-CH2Phor
Pd(OH)2 / C
MeOHOH
OH
ROH
or
Tetrahedron 4149 41552007 63 -, , 19 ,
Palladium-Catalyzed Allylic Alkylation of Secondary Nitrones.Pd
MAKI, K.; KANAI, M.; SHIBASAKI, M.
AM
R1 OBocR2
R3 R4NO2
R5R1
R2
R3R4
R5NO2
Pd cat. (1-2%)PPh3 or rac-BINAP or iPr-PHOX (6 mol%)
+DBU (10 mol%)DMSO, r.t to 50°C
R1 = Ph, R2 = R3 = H: up to 94% ee70-100% yield
NO
iPr
iPr-PHOX :
Tetrahedron 4250 42572007 63 -, , 20 ,
49
-
Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Palladium-Catalyzed Dehalogenation of Aryl Halides and αααα-Haloketones.Pd
CHEN J.; ZHANG, Y.; YANG, L.; ZHANG, X.; LIU, J.; LI, L.; ZHANG, H.
AM
XR
HR R' Br
O
R' HO
1-5 % Pd(OAc)24-20 % PPh3
alcohol, K2CO3100°C, 87-98%
alcohol, K2CO3100°C, 90-98%
1% Pd(OAc)24% PPh3
R = functional group; R' = Ar, Alkyl; X = Cl, Br, I
Tetrahedron 4266 42702007 63 -, , 20 ,
Asymmetric Allylic Alkylation using N-heterocyclic Carbene–Amino LigandsPd
FLAHAUT, A.; ROLAND, S.; MANGENEY, P.
CS
Ph
OAc
Ph
Pd[allyl)Cl]2, 3 mol%NHC-AgCl, 8.5 mol%
dimethyl malonate / NaH Ph Ph
CO2MeMeO2C
80% ee
N N
HNPh
PhEt
AgCl
i-Pr
NHC-AgCl =
Tetrahedron Asymm. 229 2362007 18 -, , 2 ,
Synthesis of Planar Chiral [2.2]paracyclophane Monophosphine Ligands Pd
ZHANG, T.-Z.; DAI L.-X.; HOU, X.-L.
CS
RCHO +
OAc [η3-(C3H5PdCl)2]
ligand 8
Et2Zn, THF
R
OH
d.r. up to 99:1ee up to 72%
PR2
(S)-8a-9
Zn
Tetrahedron Asymm. 251 2592007 18 -, , 2 ,
Microwave Assisted Asymmetric Suzuki-Miyaura and Negishi Cross-coupling ReactionsPd
GENOV, M.; ALMORýN A.; ESPINET, P.
CS
BrR
B(OH)2R
Zn 2R'
R'R[Pd]/L*, MW, 60 min. [Pd]/L*, MW, 45 min.
up to 70% eeR, R' = H, Me, OBn, OMe
R'R
up to 70% eeR, R' = H, Me, OBn, OMe
Tetrahedron Asymm. 625 6272007 18 -, , 5 ,
50
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Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Pd-Catalyzed Reaction of 1,3-Diketones with MethyleneaziridinesPd
KATHRIARACHCHI, K.K.; SIRIWARDANA, A.I.; NAKAMURA, I.; YAM AMOTO, Y.
TJ
N
R1 O
R2 R2
O+
N
O
R2
R2
R1
Pd(PPh3)4 25 mol%
benzene, 120 °C3 d
9 examples49-90%
R1 = Bn, p-MeC6H4CH2, n-HexR2 = Me, Et, -(CH2)n-
Tetrahedron Lett. 2267 22702007 48 -, , 13 ,
Pd-Catalyzed Reductive Heck CyclizationsPd
LIU, P.; HUANG, L.; LU, Y.; DILMEGHANI, M.; BAUM, J.; XIANG, T.; ADAMS, J.; TASKER, A.; LARSEN, R.; FAUL, M.M.
TJ
R1
R2
X
YZ
R3
R1
R2 YZ
R3Me
n
n 18 examples70-99%
n = 0,1X = Cl, Br
Y = NBoc, NAc, O; Z = CH2Y = CH2; Z = NBoc, O
Pd-Cat,
Base/HCO2NaDMF, 85-95 °C
Tetrahedron Lett. 2307 23102007 48 -, , 13 ,
Direct Pd-Catalyzed C-3 Arylation of IndolesPd
ZHANG, Z.; HU, Z.; YU, Z.; LEI, P.; CHI, H.; WANG, Y.; HE, R.
TJ
NH
R1
NH
R1
R2
+Br
R2Pd-Cat 5 mol%
K2CO3dioxane, reflux
Pd PP OHHO
Pd Cat. =
6 examples12-80%
Tetrahedron Lett. 2415 24192007 48 -, , 13 ,
Suzuki-Miyaura CouplingPd
A mechanistic rationale for these unusual observations is suggested.
MCMILLAN, F.M.; MCNAB, H.; REED, D.
TJ
N Br
(HO)2BCHO
+
N CO2H
N
Pd(PPh3)4 3mol%
MeO(CH2)2OMeNa2CO3/H2O20 h, reflux 94%
Tetrahedron Lett. 2401 24032007 48 -, , 13 ,
51
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Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
PMHS as a Protectant in Pd-Catalyzed Cyanation ReactionPd
MARTIN, M.T.; LIU, B.; COOLEY, B.E.; EADDY, J.F.
TJ
Br CN
Zn(CN)2Pd(OAc)2 0.9 mol%DPPF 0.12 mol%
NMP/H2O1 wt % PMHSR R
8 examples61-97%
R = CF3, OMe, COMe, NHAc
Zn
Tetrahedron Lett. 2555 25572007 48 -, , 14 ,
Selective Pd-Catalyzed AminationPd
BAEZA, A.; BURGOS, C.; ALVAREZ-BUILLA, J.; VAQUERO, J.J.
TJ
NN
N
X
Cl
Br
NN
N
X
Cl
NN H RRR
R
NaOtBuPd(OAc)2
phosphine, THF
19 examples31-90%
X = H, Cl
Tetrahedron Lett. 2597 26012007 48 -, , 14 ,
Cross-Coupling Reactions of Triarylbismuths with Aryl BromidesPd
RAO, M.L.N.; BANERJEE, D.; JADHAV, D.N.
TJ
Br3R1
+
R2
Bi
3R1
R2
Pd(OAc)2 0.1 equivPPh3 0.4 equiv
K3PO4 6 equivDMF, 90 °C, 1-2 h
25 examples49-95%
Bi
Tetrahedron Lett. 2707 27002007 48 -, , 15 ,
Pd-Catalyzed Amination of Electron-Rich IndolePd
SCHWARZ, N.; TILLACK, A.; ALEX, K.; SAYYED, I.A.; JACKSTELL, R.; BELLER, M.
TJ
N
OTBS
Me
Me
Br+ NH
R1
R2
Pd(OAc)2 1 mol%Ligand 2 mol%
LiHMDS, toluene100 °C, 24 h N
OTBS
Me
Me
NR1
R2 N
Ligand =
Padamantane
adamantane
10 examples40-91%
Tetrahedron Lett. 2897 29002007 48 -, , 16 ,
52
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Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
Preparation of S-Aryl ThioacetatesPd
LAI, C.; BACKES, B.J.
TJ
X
R
X = Br, OTf
S
RO
Me
O
Me S-K+
Pd2(dba)3Xantphos 5 mol%
iPr2NEtdioxane, MW
160 °C, 25 mn
8 examples51-91%
Tetrahedron Lett. 3033 30372007 48 -, , 17 ,
Access to Funtionalized Indoles by Cycloisomerization of 2-Propargyl AnilinesPt
The same reaction also occurs with Au(III) catalysts
CARIOU, K.; RONAN, B.; MIGNANI, S.; FENSTERBANK, L.; MALACRIA, M.
CY
OAc
N NN
PtCl2 (5 mol%),toluene, temp.
+
temp. = room temp. : 94% : 0%temp. = 110 ° C: 0% : 60%
OAcOAc
Au
Angew. Chem. Int. Ed. 1881 18842007 46 -, , 11 ,
Furan Derivatives from Rearrangement of Allenyl SulfidesPt
Depending on the substrate, the reaction is better performed with Pt, Ru or Rh based catalyst
PENG, L.; ZHANG, X.; MA, M.; WANG, J.
CY
O
PhSPh
C
MeO
H
O
Ph H
MeOSPh
PtCl2 (5 mol%) or{RuCl2(p-cymene)}2 (5 mol%)
toluene, 80 °C
73% with Pt cat.93% with Ru cat.
RuRh
Angew. Chem. Int. Ed. 1905 19082007 46 -, , 11 ,
Synthesis of Spirocyclic 3(2H)-Furanones and 3-PyrrolonesPt
BINDER, J. T.; BENEDIKT CRONE, B.; KIRSCH, S. F.; LIÉBERT, C.; MENZ, H.
BJL
OOH
R1
PtCl2 or AuCl3 catO
R1
11-93%
N
O
R1R2
R2NH2
PtCl2 cat
33-81%
Au
Eur. J. Org. Chem. 1636 16472007 -, , 10 ,
53
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Bibliographic Notebooks For Organometallic Chemistry 2007, 25, ( 3)
On Accounting for the Stereoselective Control of the Rautenstrauch ReactionPt
Computational study
SOIRANO, E.; MARCO-CONTELLES, J.
MV
OCOR
PtCl2
OCOR
OCOR
J. Org. Chem. 2651 26542007 72 -, , 7 ,
Cyclization/1,2-Migration for the Synthesis o