Photosensitized, Energy-Transfer-Mediated Cyclization of 2-(1-Arylvinyl)benzaldehydes to Anthracen-9-(10<i>H</i>)-ones

Abstract

A visible-light-induced photocatalytic intramolecular cyclization of 2-(1-arylvinyl)benzaldehydes is reported. The reaction is promoted in the presence of an Ir^III photocatalyst and an amine base at room temperature under the irradiation of blue LEDs, affording 10-methylanthracen-9(10 H)-one derivatives in moderate to good yields with tolerance to various functional groups. A series of mechanistic experiments suggest that the reaction proceeds via energy transfer from the excited Ir^III photocatalyst to the substrate to generate a diradical, which then undergoes 1,5-hydrogen shift, 6π electrocyclization, and aromatization leading to the cyclic product.