supplementary information - royal society of chemistry · supplementary information intermolecular...
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Supplementary Information Intermolecular Sulfenoamination of Alkenes with Sulfonylamides
and N-Sulfanylsuccinimides for the Synthesis of -Sulfonylamino
sulfides and Dihydrobenzothiazines
Tao Liu,a Jun Tian,b Wen-Chao Gao,*a Hong-Hong Chang,a Qiang Liu,*a Xing Li,a
and Wen-Long Weia
a College of Chemistry and Chemical Engineering, and b College of Data Science,
Taiyuan University of Technology, Taiyuan 030024, P. R. China
E-mail: [email protected]
Table of contents
Table S1. Optimization of reaction conditions for the synthesis of 11a.....S2
MS on Mechanism Study..........................................................................S3
Ring Opening of Phenyl N-tosylaziridine with Thiocresol......................S5
Crystal Structure of 4m and the Corresponding Data..............................S5
Crystal Structure of 9 and the Corresponding Data.................................S6
NMR Spectra of Products........................................................................S8
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017
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Table S1. Optimization of reaction conditions for the synthesis of 11aa
a Reaction conditions: 1a (0.2 mmol), 2e (0.3 mmol), and 3a (0.22 mmol) was subjected to the
indicated conditions. b Isolated yield.
Entry Conditions Yield (%)b
1 1) TfOH (20 mol %), CH2Cl2 (1 mL), 60 oC;
2) Pd(OAc)2 (20 mol %), BINAP (40 mol %), K2CO3 (2.5 eq), Toluene, 110 oC
0
2 1) TfOH (20 mol %), Toluene (1 mL), 60 oC;
2) Pd(OAc)2 (20 mol %), BINAP (40 mol %), K2CO3 (2.5 eq), Toluene, 110 oC
0
3 1) TfOH (20 mol %), CH2Cl2 (1 mL), 60 oC;
2) CuI (10 mol %), ethylenediamine (20 mol %), K2CO3 (2.0 eq), 1,4-Dioxane, 100 oC
0
4 1) TfOH (20 mol %), CH2Cl2 (1 mL), 60 oC;
2) Cu (1.1 eq), DMF (1 mL), N2, 120 oC
27
5 1) TfOH (20 mol %), DCE (1 mL), 60 oC;
2) Cu (1.1 eq), DMF (1 mL), N2, 120 oC
0
6 1) TfOH (20 mol %), Toluene (1 mL), 60 oC;
2) Cu (1.1 eq), DMF (1 mL), N2, 120 oC
66
7 1) TfOH (20 mol %), Toluene (0.5 mL), 60 oC;
2) Cu (1.1 eq), DMF (1 mL), N2, 120 oC
72
8 1) BF3·Et2O (20 mol %), Toluene (1 mL), 60 oC;
2) Cu (1.1 eq), DMF (1 mL), N2, 120 oC
54
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MS on Mechanism Study
Mass spectroscopy (MALDI) for the reaction of 1a with 2a
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Mass spectroscopy (MALDI) for the reaction of 1j with 2a
Ph Ph
O BF3Et2O (20 mol%)
Ph
PhO
SMe
Chemical Formula: C22H19OS+
Exact Mass: 331.12
CH2Cl2, rt
10-20 min
N
O
O
S
Me
+
1j 2a
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Synthesis of -Sulfonamino Sulfides through Ring Opening of Phenyl
N-tosylaziridine with p-Thiocresol
Ph
STol
NHTs
Ph
N
Ts
Ph
NHTs
STol +K2CO3 (1.1 equiv)p-Thiocresol (1.1 equiv)
toluene, reflux, 6 h
yield : 90%ratio = 1: 1.25
10 4a 4a'
Crystal Structure of 4m and the Corresponding Data
ORTEP drawing of 4m (CCDC 1528230); thermal ellipsoids are set at a 30%
probability level
Crystal Structure Information of 4m
Crystal data
Chemical formula C29H27ClNO3S2
Mr 537.08
Crystal system, space group Monoclinic, P21/c
Temperature (K) 290
a, b, c (Å) 10.7451 (4), 24.1196 (8), 10.5407 (4)
β (°) 100.488 (1)
V (Å3) 2686.17 (17)
Z 4
Radiation type Mo Kα
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µ (mm−1) 0.33
Crystal size (mm) 0.25 × 0.20 × 0.10
Data collection
Diffractometer Bruker APEX-II CCD diffractometer
Absorption correction Multi-scan SADABS
No. of measured, independent and observed [I > 2σ(I)] reflections
25814, 6640, 4696
Rint 0.038
(sin θ/λ)max (Å−1) 0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.157, 1.06
No. of reflections 6640
No. of parameters 327
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.32, −0.51
Crystal Structure of 9 and the Corresponding Data
ORTEP drawing of 9 (CCDC 1528231); thermal ellipsoids are set at a 30%
probability level
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Crystal Structure Information of 9
Crystal data
Chemical formula C19H23NO2S2
Mr 361.50
Crystal system, space group Monoclinic, P21/c
Temperature (K) 284
a, b, c (Å) 10.7682 (5), 18.6312 (8), 10.2412 (5)
β (°) 110.113 (1)
V (Å3) 1929.34 (15)
Z 4
Radiation type Mo Kα
µ (mm−1) 0.29
Crystal size (mm) 0.30 × 0.25 × 0.18
Data collection
Diffractometer Bruker APEX-II CCD diffractometer
Absorption correction Multi-scan SADABS
No. of measured, independent and observed [I > 2σ(I)] reflections
18068, 4730, 3414
Rint 0.031
(sin θ/λ)max (Å−1) 0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.163, 1.01
No. of reflections 4730
No. of parameters 219
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.50, −0.42
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NMR Spectra of Products
4a
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4a
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4b
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4b
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4c
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4c
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4d
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4d
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4f
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4h
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4h
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4i
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4i
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4j
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4j
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4k
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4k
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4l
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4l
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4m
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4m
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4n
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4n
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4o
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4o
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4pa+4pb
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4pa
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4pa
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4q
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4r
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9
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