Ritter-type hydrofunctionalization of alkenes provides an efficient approach for constructing C(sp3)–N bonds, but it is generally limited to amide installation at original alkene position. Herein, we report an electrooxidative palladium-hydride-catalyzed remote and divergent Ritter-type hydrofunctionalization of alkenes. In this catalytic system, a nitrilium intermediate generated at a distal position is intercepted by HFIP to furnish a HFIP-derived imidate, which serves as a branching intermediate for telescoped remote hydroamidation and hydrotetrazolation. Mechanistic studies elucidate that HFIP facilitates palladium-hydride formation, and further reveal the role of electrooxidation in governing product formation.
Park et al. (Tue,) studied this question.