Single-carbon atom transfer to α,β-unsaturated amides from N-heterocyclic carbenes.

Abstract

Single-carbon atom transfer reactions are lacking in organic synthesis, partly because of the absence of atomic carbon sources under standard solution-phase conditions. We report here that N-heterocyclic carbenes can serve as atomic carbon donors through the loss of a 1,2-diimine moiety. This strategy is applicable to single-carbon atom transfer to α,β-unsaturated amides, which can be converted into homologated γ-lactams through the formation of four single bonds to one carbon center in one operation.