Issue 1, 2017

Nickel-catalyzed direct formation of the C–S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent

Abstract

Various unsymmetrical aryl sulfides were synthesized by nickel-catalyzed C–S bond formation in good to excellent yields. The reactions employed arylsulfonyl chlorides as an aryl thiol source and Mn dust as a reducing agent. The scope and versatility of the method have been successfully demonstrated with 42 examples. Mechanistic studies revealed the existence of an intermediate disulfide substance. A catalytic cycle was proposed including a three-step reduction by Mn for the achievement of the reaction, and Ni(0) and Ni(I) species were supposed to be involved in the reaction mechanism.

Graphical abstract: Nickel-catalyzed direct formation of the C–S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent

Supplementary files

Article information

Article type
Research Article
Submitted
11 Aug 2016
Accepted
07 Oct 2016
First published
08 Oct 2016

Org. Chem. Front., 2017,4, 31-36

Nickel-catalyzed direct formation of the C–S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent

Y. Wang, X. Zhang, H. Liu, H. Chen and D. Huang, Org. Chem. Front., 2017, 4, 31 DOI: 10.1039/C6QO00451B

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