A Precise Route to Tetrasubstituted Allyl Amines via Regioselective Dicarbofunctionalization of Masked Propargyl Amines.

Abstract

Allyl amines are vital components in various biologically important molecules and play a significant role in their function. Presently, most methods are geared toward the preparation of di- and trisubstituted allyl amines, leaving a gap for the development of more versatile approaches. We herein describe an approach to yield tetrasubstituted allyl amines through palladium (Pd)-catalyzed regioselective dicarbofunctionalization of masked N-phthalimide-protected propargyl amines. The cationic Pd-intermediate in conjunction with the masked amine exerts collective control for the reaction regioselectivity. This method accommodates a wide range of alkynes, aryl boronic acids, and aryl diazonium salts offering direct access to a wide range of unusual tetrasubstituted allyl amines.