Tandem Azolation/Aromatization of Tetrahydronaphthalenes with Hydrogen Evolution via Organophotoredox/Cobalt Dual Catalysis

Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of N-(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a N-centered radical mediated C-H/N-H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.