Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

Org Lett. 2020 Nov 20;22(22):8802-8807. doi: 10.1021/acs.orglett.0c03160. Epub 2020 Oct 13.

Abstract

The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates.

Publication types

  • Research Support, Non-U.S. Gov't