A Bioinspired Catalytic Aerobic Functionalization of Phenols: Regioselective Construction of Aromatic C–N and C–O Bonds

Abstract

We report a bioinspired approach for the regioselective construction of both aromatic C–O and C–N bonds through the dehydrogenative coupling of phenols and aliphatic amines. Mechanistically, the process hinges on the ortho-oxygenation of phenols to ortho-quinones followed by aromatic C–N bond formation through a condensation/redox isomerization cascade. Overall, the process enables the regioselective formation of aromatic C–O and C–N bonds directly from C–H bonds under mild reaction conditions.