Issue 23, 2022

Copper-catalyzed regioselective C2–H chlorination of indoles with para-toluenesulfonyl chloride

Abstract

A copper-catalyzed, pyrimidine directed regioselective C–H chlorination of indoles with para-toluenesulfonyl chloride (TsCl) has been developed. The reactions proceeded smoothly in the presence of 20 mol% of Cu(OAc)2 as the catalyst and TsCl as the chlorine source, delivering C2-chlorinated indoles with structural diversity in moderate to excellent yields. Mechanistic studies suggested that single electron transfer (SET) from Cu(II) to TsCl accompanied by the release of the p-toluenesulfonyl radical and the related Cu(III)Cl species might be involved in the reactions.

Graphical abstract: Copper-catalyzed regioselective C2–H chlorination of indoles with para-toluenesulfonyl chloride

Supplementary files

Article information

Article type
Paper
Submitted
22 Apr 2022
Accepted
18 May 2022
First published
20 May 2022

Org. Biomol. Chem., 2022,20, 4815-4825

Copper-catalyzed regioselective C2–H chlorination of indoles with para-toluenesulfonyl chloride

X. Li, G. Yang, J. Gong and M. Song, Org. Biomol. Chem., 2022, 20, 4815 DOI: 10.1039/D2OB00758D

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