Issue 22, 2019

Manganese(iii) acetate-mediated direct C(sp2)–H-sulfonylation of enamides with sodium and lithium sulfinates

Abstract

A Mn(OAc)3 mediated oxidative C(sp2)–H sulfonylation of enamides and encarbamates with sodium and lithium sulfinates is reported. This operationally simple transformation provides a straightforward and highly stereoselective access to (E)-β-amidovinyl sulfones in moderate to excellent yields. The reaction proceeds readily under mild conditions at room temperature and tolerates various sensitive functional groups. This process affords exclusively (E)-configurated β-amidovinyl sulfones independent of the starting material configuration. Moreover, a direct transformation of organolithium reagents and sulfur dioxide into β-amidovinyl sulfones is described.

Graphical abstract: Manganese(iii) acetate-mediated direct C(sp2)–H-sulfonylation of enamides with sodium and lithium sulfinates

Supplementary files

Article information

Article type
Paper
Submitted
10 Ebr. 2019
Accepted
04 Mae 2019
First published
06 Mae 2019

Org. Biomol. Chem., 2019,17, 5538-5544

Manganese(III) acetate-mediated direct C(sp2)–H-sulfonylation of enamides with sodium and lithium sulfinates

P. Kramer, S. Krieg, H. Kelm and G. Manolikakes, Org. Biomol. Chem., 2019, 17, 5538 DOI: 10.1039/C9OB00825J

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