Palladium(0)-catalyzed iminohalogenation of alkenes: synthesis of 2-halomethyl dihydropyrroles and mechanistic insights into the alkyl halide bond formation.

Abstract

Although the advances on carbon halide reductive elimination have been made, the alkyl bromide and chloride analogues remain a challenge. Here, a palladium(0)-catalyzed iminohalogenation of γ,δ-unsaturated oxime esters is described, and the use of electron-poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination. Furthermore, S(N)2-type alkyl bromide and chloride reductive elimination has also been established.

DOI: 10.1002/anie.201410996