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Title: Photosensitized, energy-transfer-mediated cyclization of 2-(1-arylvinyl)benzaldehydes to anthracen-9-(10H)-ones
Authors: Ding, Wei
Ho, Chang Chin
Yoshikai, Naohiko
Keywords: Science::Chemistry
Issue Date: 2019
Source: Ding, W., Ho, C. C., & Yoshikai, N. (2019). Photosensitized, energy-transfer-mediated cyclization of 2-(1-arylvinyl)benzaldehydes to anthracen-9-(10H)-ones. Organic Letters, 21(4), 1202-1206. doi:10.1021/acs.orglett.9b00182
Journal: Organic Letters
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.
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.9b00182
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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