Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates

Jie Bai; Xiuling Cui; Hui Wang; Yangjie Wu

doi:10.1039/c4cc02693d

Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates

Chem Commun (Camb). 2014 Aug 18;50(64):8860-3. doi: 10.1039/c4cc02693d.

Authors

Jie Bai¹, Xiuling Cui, Hui Wang, Yangjie Wu

Affiliation

¹ Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou, 450052, P. R. China. cuixl@zzu.edu.cn wyj@zzu.edu.cn.

PMID: 24969096
DOI: 10.1039/c4cc02693d

Abstract

An efficient protocol for copper-catalyzed reductive cross-coupling of aryl sulfonyl chlorides with H-phosphonates has been developed. The various S-aryl phosphorothioates were afforded in up to 86% yield for 20 examples. This protocol features high efficiency, wide functional group tolerance, commercially available aryl sulfonyl chlorides as starting materials and base-free conditions.

Publication types

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

MeSH terms

Catalysis
Copper / chemistry*
Organophosphonates / chemistry
Organothiophosphorus Compounds / chemical synthesis*
Sulfinic Acids / chemistry*

Substances

Organophosphonates
Organothiophosphorus Compounds
Sulfinic Acids
sulfonyl chloride
Copper