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

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 beta-carboline synthesis. A mechanistic study suggested an irreversible nucleopalladation pathway. Hydrocarbofunctionallzation J1 examples, up to 85% yield broad substrate scope biorelevant scaffolds Immovable directing group N R tryptamine scaffolds step, while protodepalladation follows a reversible

Automated summary

The hydrocarbofunctionalization of allyl amines connected to the picolinamide directing group is developed under Pd(II) catalysis. The strategy is based on a nucleopalladation concept and can effectively produce indole derivatives. The synthetic utilities of this reaction, including the Pictet-Spengler cyclization and beta-carboline synthesis, were demonstrated. Mechanistic studies indicate that the reaction proceeds through an irreversible nucleopalladation pathway.