N-Heterocyclic carbene-catalyzed stereoselective construction of olefinic carbon-sulfur bonds via cross-coupling reaction of gem-difluoroalkenes and thiols

被引：41

作者：

Cong, Zi-Song ^{[1
]}

Li, Yang-Guo ^{[1
]}

Chen, Lei ^{[1
]}

Xing, Fen ^{[1
]}

Du, Guang-Fen ^{[1
,2
]}

Gu, Cheng-Zhi ^{[1
,3
]}

He, Lin ^{[1
,3
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Shihezi 832000, Xinjiang Uygur, Peoples R China

[2] Lab Mat Oriented Chem Engn Xinjiang Uygur Autonom, Shihezi, Peoples R China

[3] Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 18期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; DYNAMIC KINETIC RESOLUTION; INTERMOLECULAR STETTER REACTION; INTRAMOLECULAR BENZOIN REACTION; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITIONS; TRANSESTERIFICATION/ACYLATION REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; GAMMA-BUTYROLACTONES;

D O I：

10.1039/c7ob00599g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel organocatalytic olefinic carbon-sulfur bond forming reaction was developed. Under the catalysis of 10 mol% stable N-heterocyclic carbene, thiols undergo direct nucleophilic substitution reaction with gem-difluoroalkenes to produce alpha-fluorovinyl thioethers in high yields with excellent Z-selectivity. In this process, bases are not necessary.

引用

页码：3863 / 3868

页数：6

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