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 condition via a radical process. A broad substrate scope and excellent functional group tolerance is presented. Moreover, a cascade alkylsulfonylation/cyclization reaction of N-methacryloyl enamides occur smoothly, giving rise to various alkylsulfonylated pyrrolidones.