Palladium(II)-Catalyzed Regioselective Hydrocarbofunctionalization of N-Alkenyl Amides: Synthesis of Tryptamine Derivatives.

Abstract

The hydrocarbofunctionalization of allyl amines connected to the picolinamide directing group is developed under Pd(II) catalysis. The strategy is grounded on a nucleopalladation concept, and a wide range of indoles effectively participated to produce valuable tryptamine derivatives in high yields. Synthetic utilities were showcased through the substrate diversification bearing bioactive core, Pictet-Spengler cyclization, and β-carboline synthesis. A mechanistic study suggested an irreversible nucleopalladation step, while protodepalladation follows a reversible pathway.