Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling

Sadananda Ranjit; Zhongyu Duan; Pengfei Zhang; Xiaogang Liu

doi:10.1021/ol101729k

Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling

Org Lett. 2010 Sep 17;12(18):4134-6. doi: 10.1021/ol101729k.

Authors

Sadananda Ranjit¹, Zhongyu Duan, Pengfei Zhang, Xiaogang Liu

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

PMID: 20726572
DOI: 10.1021/ol101729k

Abstract

A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of CuI and Cs(2)CO(3), a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon / chemistry*
Catalysis
Copper / chemistry*
Decarboxylation
Molecular Structure
Stereoisomerism
Sulfhydryl Compounds / chemistry
Sulfides / chemical synthesis*
Sulfur / chemistry*
Vinyl Compounds / chemical synthesis*

Substances

Sulfhydryl Compounds
Sulfides
Vinyl Compounds
Sulfur
Carbon
Copper