Metalated nitrile and enolate chlorinations

Abstract

(Figure presented) Metalated nitriles and enolates rapidly and efficiently abstract chlorine from 2-chloro-2-fluoro-2-phenylacetonitrile to afford a diverse range of chloronitriles and chloroesters. The method provides the first general anionic chlorination of alkylnitriles, tolerates numerous functional groups, and addresses the challenge of synthesizing α-chloronitriles under mild conditions. © 2010 American Chemical Society.