PubAg

Main content area

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

Author:
Ding, Wei, Ho, Chang Chin, Yoshikai, Naohiko
Source:
Organic letters 2019 v.21 no.4 pp. 1202-1206
ISSN:
1523-7052
Subject:
ambient temperature, aromatization, cyclization reactions, energy transfer, irradiation, moieties, organic compounds, photocatalysis, photocatalysts
Abstract:
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.
Agid:
6310525