Phosphine Catalyzed α-Arylation of Enones and Enals Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis

Abstract

Exposure of enones and enals to 20 mol % tributylphosphine in the presence of triarylbismuth(V) dichlorides results in regiospecific aryl transfer to the alpha-position of the enone or enal pronucleophile. These results represent the first examples of enolate arylation under the conditions of nucleophilic catalysis.