Photosensitized, energy-transfer-mediated cyclization of 2-(1-arylvinyl)benzaldehydes to anthracen-9-(10H)-ones

• Main Authors: Ding, Wei, Ho, Chang Chin, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry; Energy Transfer; Cyclization
• Online Access: https://hdl.handle.net/10356/143359
• Institution: Nanyang Technological University

A visible-light-induced photocatalytic intramolecular cyclization of 2-(1-arylvinyl)benzaldehydes is reported. The reaction is promoted in the presence of an IrIII 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 IrIII photocatalyst to the substrate to generate a diradical, which then undergoes 1,5-hydrogen shift, 6π electrocyclization, and aromatization leading to the cyclic product.