chemistry letters...1346 skeletal silica nanoparticles prepared by control of reaction polarity we...

Chemistry Lettershttp://www.csj.jp/journals/chem-lett/

Vol.40 No.12 CMLTAGDecember, 2011 ISSN 0366-7022

Copyright © 2011 The Chemical Society of Japan

Highlight Review

1316 Arylethynylanthraquinone and Bis(aryleth-ynyl)anthraquinone: Strong DonorAcceptorInteraction and Proton-induced Cyclizationto Form Pyrylium and Dipyrylium Salts

Ryota Sakamoto, Koya Prabhakara Rao, andHiroshi Nishihara*doi:10.1246/cl.2011.1316

Letter

1327 Rapid and Continuous Polyol Process forPlatinum Nanoparticle Synthesis Using aSingle-mode Microwave Flow Reactor

Reactor tube

Platinum nanoparticles

MW cavity

Frequencyadjustedmicrowave

Electric field intensity

Low High

10.0 10.0

40.0 40.0

70.0 70.0

100.0100.0

130.0130.0

160.0160.0

190.0190.0

Flow

dir

ectio

n

Masateru Nishioka,* Masato Miyakawa, YoheiDaino, Haruki Kataoka, Hidekazu Koda, KoichiSato, and Toshishige M. Suzuki*doi:10.1246/cl.2011.1327Electronic Supporting Information

1330 Insights into Uranyl Ion Binding to Ubiq-uitin from Molecular Modeling and Dynam-ics Simulations

A computer modeling struture of uranyl−ubiquitin complex (UO2

2+−Ub) overlapps with Ub (in gray).

Ying-Wu Lin,* Chang-Ming Nie, and Li-FuLiaodoi:10.1246/cl.2011.1330

http://www.csj.jp/journals/chem-lett/http://dx.doi.org/10.1246/cl.2011.1316http://dx.doi.org/10.1246/cl.2011.1327http://dx.doi.org/10.1246/cl.2011.1330

1332 Generation of Brønsted Acid Sites on Alu-mina-supported Tantalum(V) Oxide Cal-cined at 1223K

1223 K

+

Ta2O5/Al2O3

Brønsted acid site

OCH3

OCH3OH

Tomoyuki Kitano, Shota Okazaki, TetsuyaShishido,* Kentaro Teramura, and TsunehiroTanaka*doi:10.1246/cl.2011.1332Electronic Supporting Information

1335 ONOFF Switching of the SolvatochromicBehavior of a Copper(II)Hydrazone Com-plex Induced by Protonation/Deprotonation

Mee Chang, Atsushi Kobayashi,* Ho-CholChang, Kiyohiko Nakajima, and Masako Kato*doi:10.1246/cl.2011.1335Electronic Supporting Information

1338 Protein Nanotube Arrays Immobilized onSolid Substrates: Molecular Trap in AqueousMedium

10 µm 1 µm

Incubation

FITC-biotin

Ryunosuke Kato and Teruyuki Komatsu*doi:10.1246/cl.2011.1338Electronic Supporting Information

1340 Quaternary-ammonium-bearing AromaticSurfactants: Effect of the Alkyl ChainPositions on Their Micelle and DNA-com-plex Structures

QAmp12

+DNA

QAmm12

+DNA

The isomerism in QAmm and QAmp induces dramatic difference in both micellar assembling and DNA-complexed structures. The former showed a hexagonally packed cylinder, while the latter a lamella. After complexation with DNA, both show a sandwiched lamella, but the spacing is different.

Takuma Matsuo, Shota Fujii, Yumi Kamikawa,Tomoki Nishimura, Yusuke Sanada, ShinichiMochizuki, and Kazuo Sakurai*doi:10.1246/cl.2011.1340Electronic Supporting Information

1343 Synthesis and Stereochemical Behavior of aNew Chiral Oxa[7]heterohelicene

OH

I I

TMS H

HO OH

Sonogashira-coupling

(rapid inversion of helical ring)

DMSO, rt

64%

O O

Oxa[7]heterohelicene

Pd(OAc)2 (10 mol%)air (O2)Ryo Irie,* Akihiro Tanoue, Suguru Urakawa,

Tatsushi Imahori, Kazunobu Igawa, TaisukeMatsumoto, Katsuhiko Tomooka, ShinsukeKikuta, Tatsuya Uchida, and Tsutomu Katsukidoi:10.1246/cl.2011.1343Electronic Supporting Information

Chemistry Letters Vol.40, No.12 (2011)C-126

http://www.csj.jp/journals/chem-lett/Copyright © 2011 The Chemical Society of Japan

http://dx.doi.org/10.1246/cl.2011.1332http://dx.doi.org/10.1246/cl.2011.1335http://dx.doi.org/10.1246/cl.2011.1338http://dx.doi.org/10.1246/cl.2011.1340http://dx.doi.org/10.1246/cl.2011.1343http://www.csj.jp/journals/chem-lett/

1346 Skeletal Silica Nanoparticles Prepared byControl of Reaction Polarity

We report skeletal silica nanoparticles using cubic template whose surface is coated by surfactant. The controlling factors, (a) high acidity of silanol compared to that of surfactant, (b) low affinity between surfactant and organic medium, and (c) high surface energy of vertex and edge of the template, are associated to obtain such structures.

Chika Takai, Masayoshi Fuji,* and KyoichiFujimotodoi:10.1246/cl.2011.1346Electronic Supporting Information

1349 Spontaneous Conversion of 3-Alkyl-substi-tuted 3-Hydroperoxypyrrolidine-2,4-dionesinto 5-Alkyl-5-hydroxyoxazolidin-4-ones

Md. Aminul Haque, Hayato Ishikawa, andHiroshi Nishino*doi:10.1246/cl.2011.1349

1352 Diameter Control of Silver Nanowires byChloride Ions and Its Application as Trans-parent Conductive Coating (1) nAgNO3 + KCl 3 + (n-1)NO3- + (n-1)Ag+

Ag+ + Cl-

Ag0 seeds

Ag0 nucleiEG

Ag0 nanowires

(2) Ag0 nuclei Spray Coating

Transparent Conductive Coating

AgCl + KNO

Ya-Hsing Chang, Yu-Chieh Lu, and Kan-SenChou*doi:10.1246/cl.2011.1352

1354 Assembling and Patterning of Diatom Frus-tules onto PDMS Substrates Using Photo-assisted Chemical Bonding

After ultraviolet irradiation, the –OSi(CH3)2O− groups of PDMS surface were changed into –O4Si(OH)4−n −, and more Si−OH groups generated. The active Si−OH groups on contact surface of PDMS and diatom may form a –Si–O–Si– crosslinking structure via condensation reaction. After 48 h, the patterned frustules were firmly bonded onto the PDMS surface.

Yu Wang, Junfeng Pan, Jun Cai, Aobo Li,Mingli Chen, and Deyuan Zhang*doi:10.1246/cl.2011.1354Electronic Supporting Information

1357 p-Aminophenyl Alkyl Ether-based 19FMRIProbe for Specific Detection and Imaging ofHypochlorite Ion

19F MRI probe for the specific detection and imaging of –OCl.

Tomohiro Doura, Qi An, Fuminori Sugihara,Tetsuya Matsuda, and Shinsuke Sando*doi:10.1246/cl.2011.1357Electronic Supporting Information

Chemistry Letters Vol.40, No.12 (2011) C-127



1360 Raman, UVvis, and CD SpectroscopicStudies of Dodecameric Oxyhemocyaninfrom Carcinus aestuarii

Niels H. Andersen, Giorgio Zoppellaro, LuigiBubacco, Luigi Casella, and K. KristofferAndersson*doi:10.1246/cl.2011.1360Electronic Supporting Information

1363 Refractive Index Changes in Polymers Bear-ing Pendant Active Ester Groups by Ther-mal Rearrangement Reaction

C

S

O N

C

S

O N

C O

S

O N

n

SO

N

C

SO

N

C

Δn ≈ +0.01

O OO O Δ

Makoto Miyasaka, Ayano Higurashi, andAtsushi Kameyama*doi:10.1246/cl.2011.1363Electronic Supporting Information

1366 pH- and Temperature-induced Crystalliza-tion of Aqueous Dispersions of PositivelyCharged Poly(styrene-co-2-vinylpyridine)Particles

Ryota Nagano, Akiko Toyotama,* and JunpeiYamanakadoi:10.1246/cl.2011.1366

1368 In Situ Observation ofWacker-type ReactionSystem in Organic Solvent by X-ray Absorp-tion Fine Structure (XAFS) Analysis

Pd(OCOCF3)2

Cu(OCOCF3)2

Homogeneous Reaction System

X-ray from Synchrotron Radiation Source

In-situ Observation

1-OcteneShin-ichi Okuoka, Takeo Akatsuka, YasuyukiMiyoshi, Aki Tsukajima, Makoto Saito, andKoji Yonehara*doi:10.1246/cl.2011.1368

1371 Fast Synthesis of Highly Dispersed AnataseTiO2 Nanocrystals in a Microfluidic Reactor

Monodispersed anatase TiO2 nanocrystals were synthesized by a microfluidic reactor within a time as short as one or two minutes. The results showed that the 5.0-nm-sized nanocrystals possessed a high specific surface area of 314.5 m2 g−1 with both mesopores and micropores existent.

Li Zhang, Yaogang Li, Qinghong Zhang,*Guoying Shi, and Hongzhi Wang*doi:10.1246/cl.2011.1371Electronic Supporting Information




1374 Electrooxidation of Formic Acid at Plati-numGold Nanoparticle-modified Electrodes

Platinum nanoparticles have been electrodeposited on gold nanoparticle (AuNP)-modified glassy carbon (GC) substrate to serve as anodic electrocatalyst for the electrooxidation of formic acid. Interestingly, the assembling procedure of AuNPs on the GC substrate influenced greatly the degree of the catalytic enhancement for this reaction. The continuity interruption of Pt sites played a significant role for the observed enhancement.

Islam M. Al-Akraa, Ahmad M. Mohammad,Mohamed S. El-Deab,* and Bahgat E.El-Anadoulidoi:10.1246/cl.2011.1374

1376 Urea-induced Direct Synthesis of Nanostruc-tured ¡-Ni(OH)2 on Nickel Foam

A thermodynamically controlled process leads to the formation of urchin-like α-Ni(OH)2 spheres that are composed of nanofibers with average diameter of less than 20 nm. The nanostructured Ni(OH)2 displayed a good electrochemical activity with a maximum specific capacitance of 103 mA h g−1 at a current density of 2.5 A g−1.

Sa Lv and Shuangxi Xing*doi:10.1246/cl.2011.1376Electronic Supporting Information

1378 A Novel Approach to Branched Polymers viaLatent Thiol Chain-transfer Polymerization

A novel branched polymerization using a latent chain-transfer monomer.

Jinqiang Jiang,* Xiuli Jia, Xin Chen, YiwuZong, Hongwu Zhang, Ling Lin, Xiaoya Liu,and Mingqing Chen*doi:10.1246/cl.2011.1378Electronic Supporting Information

1381 Temperature-swing Microfluidic Separationof Uranyl Ions Using ThermoresponsiveCopolymer Brushes

Catch-and-release of uranyl ions onto the microfluidic channels.

Takehiko Tsukahara* and Naokazu Idotadoi:10.1246/cl.2011.1381

1383 Fast Preparation of High-performance Zeo-lite T Membranes in Fluoride Media

Zeolite T membranes with high pervaporation performance were formed rapidly on seeded mullite tubes in fluoride media in only 6 h. The as-synthesized membranes showed a high water-selective permeation toward water/alcohol mixtures.

19F MAS NMR spectra of zeolite T powder by in situ hydrothermal synthesis

Rongfei Zhou, Fei Zhang, Na Hu, XiangshuChen,* and Hidetoshi Kitadoi:10.1246/cl.2011.1383Electronic Supporting Information




1386 Rapid Access to 3-Aryltetralin Skeleton viaC(sp3)H Bond Functionalization: Investiga-tion on the Substituent Effect of AromaticRing Adjacent to CH Bond in HydrideShift/Cyclization Sequence

The concise construction of 3-aryltetralin skeleton via hydride-shift-mediated C–H bond functionalization was achieved. In this process, the benzylic [1,5]-H shift occurred smoothly to furnish tetralin derivatives in good to excellent chemical yields. The electronic and steric properties of the aromatic ring adjacent to the C–H bond influenced significantly the reactivity of this transformation.

CH2

Ar CH2

Ar

Sc(OTf)3

N

ClCH2CH2Clreflux

H

H

CH2

Ar

H

[1,5]-H Shift

C – C bondformation

criticalelectronic factor

NN

O

O

O

N

O

O O

NN

O O

O

Sc3+

ArHCl OMeMe

30 mol%88%, 24 h

5 mol%94%, 24 h

1 mol%95%, 10 h

0.5 mol%90%, 12 h

cat.

Keiji Mori, Shosaku Sueoka, and TakahikoAkiyama*doi:10.1246/cl.2011.1386Electronic Supporting Information

1389 Fire-shielding Properties of Flexible, Trans-parent LaponitePEG Hybrid Film

Kazuhiro Shikinaka, Kazuto Aizawa, YoshihitoOsada, and Kiyotaka Shigehara*doi:10.1246/cl.2011.1389Electronic Supporting Information

1392 Carbazole and Hydroxy Groups-taggedPoly(aspartic acid) Scale Inhibitor for Cool-ing Water Systems

In order to conveniently monitor the concentration of poly(aspartic acid) (PASP) used as a green scale inhibitor in cooling water systems, and to improve calcium phosphate inhibition, carbazole and hydroxy groups-tagged PASP (CHGTPASP) was synthesized by ring-opening reaction of N-(2,3-epoxylpropyl)carbazole (EPC) with partially ethanolamine-modified polysuccinimide (PEAMPSI) followed by alkaline hydrolysis. CHGTPASP has good Ca3(PO4)2 and CaCO3 inhibition and its fluorescence intensity (Fi) is good linear to concentration. These multifunctional properties are of importance in industrial water processing economically and environmentally.

Li-Jun Gao, Jiu-Ying Feng,* Bei Jin, Qiu-NaZhang, Tian-Qin Liu, Yang-Qing Lun, andZhao-Jun Wudoi:10.1246/cl.2011.1392Electronic Supporting Information

1395 A Nonadiabatic Ab Initio Dynamics Studyon Rhodopsin and Its Analog Isorhodopsin:Chemical Dynamics Reasons behind Selec-tion of Rhodopsin by Life

Wilfredo Credo Chung,* Shinkoh Nanbu, andToshimasa Ishidadoi:10.1246/cl.2011.1395Electronic Supporting Information

1398 SR-XRF Imaging of Cs Highly Accumulatedin Vegetables

Cabbage (symbol A) and two other vegetables accumulate Cs to more than 10000 ppm. The concentrations and ditribution of Cs in these plants were revealed by in vivo synchrotron radiation X-ray fluorescence imaging.

A B C

Plant name A:Brassica oleracea var. capitata, B:Lactuca sativa, C:Brassica campestris var. perviridisIzumi Nakai,* Nahoko Oda, and Yasuko Teradadoi:10.1246/cl.2011.1398




1400 Color Evolution and Thermal Behavior ofSilica (SiO2)- and Zircon (ZrSiO4)-coatedNano ¡-Fe2O3 Pigments

Ri Yu, Jae-Hwan Pee, Kyung Ja Kim, andYooJin Kim*doi:10.1246/cl.2011.1400Electronic Supporting Information

1402 Volatile Organic Compound Sensing by GoldNanoparticles Capped with Calix[4]areneLigand

Mutsumi Kimura,* Mei Yokokawa, Seiko Sato,Tadashi Fukawa, and Takashi Miharadoi:10.1246/cl.2011.1402Electronic Supporting Information

1405 Direct Synthesis of Phenol from Benzeneover Platinum-loaded Tungsten(VI) OxidePhotocatalysts with Water and MolecularOxygen

Osamu Tomita, Ryu Abe,* and Bunsho Ohtanidoi:10.1246/cl.2011.1405

1408 Tin Tetra(tert-butoxide) with AcidBase Ad-ditives: Valid Catalyst Precursors for DirectSynthesis of Dimethyl Carbonate from CO2and CH3OH

Sn(Ot-Bu)4 is a user-friendly precatalyst for the direct synthesis of dimethyl carbonate from CO2 and MeOH. It is far more active than the conventional Bu2Sn(OMe)2 catalysts. The addition of acid and/or base cocatalysts as well as optimization of the CO2 pressure improved the catalytic activity.

Yoichi Masui, Shunsuke Haga, and MakotoOnaka*doi:10.1246/cl.2011.1408Electronic Supporting Information

1411 Nanoscale Laser Processing of Hollow SilicaMicrobeads Assisted by Surface PlasmonResonance of Gold Particles

Au

SiO2 PoreVoid

Laser irradiation(532 nm)

Au −SiO2 composite shell particle

hollow SiO2shell particle

Koji Furukawa, Tatsuya Kameyama, Ken-ichiOkazaki, Takayuki Yako, Masashi Otsuki,Yasuyuki Tsuboi,* and Tsukasa Torimoto*doi:10.1246/cl.2011.1411Electronic Supporting Information




1414 Novel Synthetic Method for Metalloporphyr-ins with Inorganic Metal Salts in High-temperature Water

Takafumi Sato, Katsutoshi Ebisawa, Satoshi Ito,Kiwamu Sue, and Naotsugu Itoh*doi:10.1246/cl.2011.1414Electronic Supporting Information

1417 Synthesis and Enhanced Radical ScavengingActivity of a Conformationally ConstrainedEpigallocatechin Analogue

O

OH

HO

OH

OHOH

O

O

HO

OH

OHOH

O

epigallocatechin

OH OHKohei Imai, Ikuo Nakanishi, Kazunori Anzai,Toshihiko Ozawa, Naoki Miyata, Shiro Urano,Haruhiro Okuda, Asao Nakamura, and KiyoshiFukuhara*doi:10.1246/cl.2011.1417

1420 Glycine Amino Acid Transport inside theNanopores of Lysozyme Protein Crystal

0

5

10

15

20

0 0.5 1 1.5

r/nm

g (

r)

Glycine

Glycine 1 unit cell Lysozyme

Nafiseh Farhadian,* Kourosh Malek, MojtabaShariaty-Niassar, and Ali Magharidoi:10.1246/cl.2011.1420

1423 AC Electrochemical Stability of IonicLiquids AC electrochemical windows of ionic liquids were studied and were found to be much wider

than the DC case.

Fulong Yang, Zuopeng Li, Shiguo Zhang,Qinghua Zhang, Xiaodong Hu, XiaopingZhang,* and Youquan Deng*doi:10.1246/cl.2011.1423Electronic Supporting Information

1426 Softness Evaluation of Silicone Elastomers

x / cm x / cm

y /

cm

y /

cm

We evaluated the softness of various silicone elastomers installed on a tactile evaluation system. The softness of the elastomers was reflected by the vertical force when subjects pushed the elastomers with their fingers. The moving behavior depended on the elastic properties of the contacted objects; namely, a pushing pattern and sliding pattern were observed for the soft and hard elastomers, respectively.

Yoshimune Nonomura,* Takehito Baba,Takaaki Miyashita, and Takashi Maenodoi:10.1246/cl.2011.1426




1428 Synthesis and Lithium Storage Properties ofNiO@TiO2 Nanotube Heterojunction Arrays

Well-aligned TiO2 nanotube arrays were fabricated via anodization on Ti foil. Pulse current technique was employed to deposit metallic Ni into TiO2 nanotube arrays and realize a secondary hollow tubular structure. Subsequent annealing converted Ni into NiO and retained this novel tube-in-tube architecture. Characterizations had confirmed this point. Besides, electrochemical tests manifested that NiO@TiO2 nanotube arrays was a promising anode material for Li-ion batteries.Lili Wang, Shichao Zhang,* and Xiaomeng Wu

doi:10.1246/cl.2011.1428

1431 Oxygen Atom Transfer from Peroxide Inter-mediates to Fullerenes

Photoreaction of C60 and C70 with adamantylideneadamantane or sulfide under oxygen flow gives fullerene epoxide together with adamantylideneadamantane epoxide or sulfoxide via peroxide intermediates.

Yutaka Maeda, Yasuyuki Niino, Takuya Kondo,Michio Yamada, Tadashi Hasegawa, andTakeshi Akasaka*doi:10.1246/cl.2011.1431Electronic Supporting Information



http://dx.doi.org/10.1246/cl.2011.1428http://dx.doi.org/10.1246/cl.2011.1431http://www.csj.jp/journals/chem-lett/

1434 Sequential SuzukiMiyaura Cross-couplingReactions of 4-Halopyrazolyl MIDA 3-Boro-nates: A Modular Synthetic Entry to 3,4-Bis(hetero)aromatic Pyrazoles

4-Iodopyrazolyl MIDA 3-boronates, readily accessible via sydnone cycloaddition of ethynyl MIDA boronate and subsequent iodination, are valuable scaffolds for the orthogonal functionalization of the pyrazole ring by means of Suzuki cross-coupling reactions.

O

NN

R

OBmida

+N

N

Bmida

R

I

NN

(Het)Ar2

R

(Het)Ar1 Suzukicross-coupling

1/ (Het)Ar1B(OH)22/ (Het)Ar2I

1/ [3+2] (-CO2)

2/ NIS/TFAThierry Delaunay, Mazen Es-Sayed, Jean-PierreVors, Nuno Monteiro,* and Geneviève Balme*doi:10.1246/cl.2011.1434Electronic Supporting Information

1437 Diacenaphtho[1,2-b;1¤,2¤-d]silole and -pyrroleSi

Ph PhN

PhBr Br

Yoshiharu Nagasaka, Chitoshi Kitamura,Hiroyuki Kurata, and Takeshi Kawase*doi:10.1246/cl.2011.1437Electronic Supporting Information

1440 Stereoselective Synthesis of AllylsilanesBearing Tetrasubstituted Olefin via 2,2-Diborylethylsilane

Me3SiBpin

BpinLTMPTHF, 0 °C, 5 min

thenPh

BpinMe3Si

Me

Me

BpinMe3Si

Ph

+

Ph

O

Me 98%, >99/1Kohei Endo,* Akira Sakamoto, TakahiroOhkubo, and Takanori Shibata*doi:10.1246/cl.2011.1440Electronic Supporting Information

1443 Selective Dimerization of Aryl-substitutedTerminal Alkynes on Bis(indenyl)zircono-cene Derivatives

Ar

[(Ind)3ZrH]or

[(Ind)2Zr(CO) ]22 (Ind)2Zr

A

Ar

(Ind)2Zr

Ar

(Ind)2Zr

ArAr

Ar

+

Not obtained

r

Shenyong Ren, Takashi Seki, David Necas,Hiroyuki Shimizu, Kiyohiko Nakajima,Ken-ichiro Kanno, Zhiying Song, and TamotsuTakahashi*doi:10.1246/cl.2011.1443Electronic Supporting Information

1445 Synthesis of Aromatic Polyketones Bearing1,1¤-Binaphthyl-2,2¤-dioxy Units throughSuzukiMiyaura Coupling Polymerization

(S)-1

HO

O

FI

K2CO3

DMF, 150 °C, 24 h

2A(p-I)2B(m-I)

O O

OO

II

φBO

O O

O

10 mol% Pd(OAc)220 mol% PPh3Bu4NOAcK2CO3MS4A

dioxane, 100 °C, 1 h

O O

OO

φ

n

3m,3p

4Am, 4Ap, 4Bm, 4Bp

MeO

OMe

MeO

OMe

3m

φ:

B

3p

OH

Katsuya Maeyama,* Tadashi Tsukamoto,Masanori Suzuki, Shuhei Higashibayashi, andHidehiro Sakuraidoi:10.1246/cl.2011.1445Electronic Supporting Information




1447 Synthesis of Co-oligomers of ThiopheneDerivatives from Oligoynes via Zircona-cyclopentadiene

ZrCp Cp

T TZr

Cp Cp

TTT TX

T TX

TTT TX: C=C or S

"[Cp2Zr]"

TT TTTTS

T:

Debabrata Payra, Zhiyi Song, Ken-ichiroKanno, and Tamotsu Takahashi*doi:10.1246/cl.2011.1447Electronic Supporting Information

1450 Cross Coupling on Gold Nanoparticles.Effect of Reinforced Affinity of OrganicGroup with Bipedal Thiol

S

S(CH2)11O Aryl

S

S(CH2)11O I

Aryl(RO)2B

[Pd(t -Bu3P)2]

K2CO3(aq)rt to 60 °C

Au Au

bipedal thiol-cappedgold nanoparticle

no aggregationAtsushi Sugie, Kenta Kumazawa, TomomiHatta, Kiyoshi Kanie, Atsushi Muramatsu, andAtsunori Mori*doi:10.1246/cl.2011.1450Electronic Supporting Information

1453 Diaryl Ketone Synthesis by [RuHCl(CO)-(PPh3)3]-catalyzed Coupling Reaction ofArylboronic Acids with Aryl Aldehydes

+Ar2H

O

Ar2

O[RuHCl(CO)(PPh3) ]3B(OH)2Ar1

Ar1

Takahide Fukuyama,* Hiromi Okamoto, andIlhyong Ryu*doi:10.1246/cl.2011.1453

1456 Protonation-induced Cyclization of 1,8-Bis(arylethynyl)anthraquinones: Monopyry-lium Salt Formation and Intensification ofDonorAcceptor Interaction

Koya Prabhakara Rao, Mio Kondo, RyotaSakamoto, Tetsuro Kusamoto, Shoko Kume,and Hiroshi Nishihara*doi:10.1246/cl.2011.1456Electronic Supporting Information

1459 A Forgotten Olefin: A Convenient One-potCascade Reaction Involving SuzukiMiyaura and MizorokiHeck Couplings toForm (E)-1,2-Di(pyren-1-yl)ethylene

BO

O

HH

H

R

Br

R

HH

R

R0.5 equiv

Grubbs 2ndgeneration catalyst

Ken-ichi Yamashita, Keisuke Kimura, ShinTazawa, Motoko S. Asano, and Ken-ichiSugiura*doi:10.1246/cl.2011.1459Electronic Supporting Information



chemistry letters...1346 skeletal silica nanoparticles prepared by control of reaction polarity we...

Documents