Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Abstract

Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogenbased nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.