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Issue 1, 2017
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Nickel-catalyzed direct formation of the C–S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent

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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

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Publication details

The article was received on 11 Aug 2016, accepted on 07 Oct 2016 and first published on 08 Oct 2016


Article type: Research Article
DOI: 10.1039/C6QO00451B
Citation: Org. Chem. Front., 2017,4, 31-36
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    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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