Synthesis of α-sulfenylated carbonyl compounds via combining a gold-catalyzed rearrangement and a photoinduced nickel-catalyzed Giese reaction

Abstract

A general process for synthesizing α-sulfenylated carbonyl compounds has been developed, involving a two-step procedure. This protocol employs a gold-catalyzed rearrangement of propargylic sulfoxides followed by a visible-light-induced nickel-catalyzed Giese reaction of the resulting α-thioenones with DHPs or α-silylamines to afford keto thioethers in moderate to good yields. Furthermore, this transformation exhibits compatibility with diverse functional groups. α-Sulfenylated carbonyl products are versatile intermediates, suitable for late-stage structural modification.