Issue 63, 2024

Metal- and additive-free β-C(sp2)–H decarboxylative alkylsulfonylation of enamides from phenyliodine(iii) dicarboxylates and sulfur dioxide

Abstract

A green process for the direct C(sp2)–H decarboxylative alkylsulfonylation of enamides under metal- and additive-free conditions is reported. This reaction employs phenyliodine(III) dicarboxylates as the alkyl radical precursors and DABCO·(SO2)2 as the sulfur dioxide surrogate. Diverse (E)-alkylsulfonyl enamides are generated in moderate to good yields with high stereoselectivity under extremely mild conditions via a radical process. A broad substrate scope and excellent functional group tolerance are presented. Moreover, a cascade alkylsulfonylation/cyclization reaction of N-methacryloyl enamides occurs smoothly, giving rise to various alkylsulfonylated pyrrolidones.

Graphical abstract: Metal- and additive-free β-C(sp2)–H decarboxylative alkylsulfonylation of enamides from phenyliodine(iii) dicarboxylates and sulfur dioxide

Supplementary files

Article information

Article type
Communication
Submitted
13 Jun 2024
Accepted
27 Jun 2024
First published
28 Jun 2024

Chem. Commun., 2024,60, 8212-8215

Metal- and additive-free β-C(sp2)–H decarboxylative alkylsulfonylation of enamides from phenyliodine(III) dicarboxylates and sulfur dioxide

W. Li, C. Wang, T. Zhu, G. Liu and J. Wu, Chem. Commun., 2024, 60, 8212 DOI: 10.1039/D4CC02865A

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