Issue 2, 2020

Metal- and solvent-free direct C–H thiolation of aromatic compounds with sulfonyl chlorides

Abstract

A simple, efficient and green method for the direct thiolation of aromatic compounds using commercially available sulfonyl chlorides as the sulfur source was developed under metal- and solvent-free conditions. The C–S bond was constructed via direct C–H functionalization of diverse aromatic compounds under an oxygen atmosphere. In this process, various diaryl sulfides were synthesized in moderate to excellent yields. This protocol shows a broad substrate scope and good functional group tolerance. Moreover, a gram-scale experiment was also conducted to prove the prospect of this method for the scale-up synthesis of diaryl sulfides. Mechanistic studies indicate that this procedure probably undergoes a radical pathway.

Graphical abstract: Metal- and solvent-free direct C–H thiolation of aromatic compounds with sulfonyl chlorides

Supplementary files

Article information

Article type
Paper
Submitted
28 Sep 2019
Accepted
25 Nov 2019
First published
26 Nov 2019

Green Chem., 2020,22, 427-432

Metal- and solvent-free direct C–H thiolation of aromatic compounds with sulfonyl chlorides

F. Zhao, Q. Tan, D. Wang and G. Deng, Green Chem., 2020, 22, 427 DOI: 10.1039/C9GC03384J

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