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(10H)-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, 6πelectrocyclization, and aromatization leading to the cyclic product.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry