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

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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

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Publication details

The article was received on 10 Apr 2019, accepted on 04 May 2019 and first published on 06 May 2019


Article type: Paper
DOI: 10.1039/C9OB00825J
Org. Biomol. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB00825J

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