Csp³−P^III Bond Formation via Cross‐Coupling of Umpolung Carbonyls with Phosphine Halides Catalyzed by Nickel

Abstract

A novel method for the formation of Csp³ -P^III bonds via the nickel-catalyzed cross-coupling of Umpolung carbonyls and phosphine chlorides is reported herein. This process leads to a series of alkylphosphines, which are characterized as sulfides or borane-phosphine complexes after undergoing further transformation with moderate to good yields. Invaluable free alkylphosphines can be easily obtained by desulfurization or deboration of the products. A possible mechanistic pathway is also discussed. This report represents the first example of using renewable carbonyls as latent organometallic reagent surrogates for cross-coupling with heteroatom electrophiles.