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 6 2024
Accepted
27 6 2024
First published
28 6 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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