Assembly of Diverse Allenes via Activator-Free Palladium-Catalyzed Regioselective γ-Arylation of Propargylamines with Boronic Acids

Abstract

Controlling the reaction selectivity to achieve a precision synthesis is a constant concern for chemists. Here, we report a palladium-catalyzed deaminative coupling of propargylamines with arylboronic acids to generate allene skeletons. Importantly, this approach allows the regioselective γ-arylation of unactivated propargyl tertiary amines to access various allenes in the absence of amino-activating reagents. We present a wide range of propargylamines and boronic acids and demonstrate the synthetic application of the target products to construct valuable compounds.