Please use this identifier to cite or link to this item:
https://hdl.handle.net/10356/143359
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. | URI: | https://hdl.handle.net/10356/143359 | ISSN: | 1523-7060 | DOI: | 10.1021/acs.orglett.9b00182 | Schools: | School of Physical and Mathematical Sciences | 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 https://doi.org/10.1021/acs.orglett.9b00182 | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Journal Articles |
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Photosensitized, Energy-Transfer-Mediated Cyclization of 2-(1-Arylvinyl)benzaldehydes to Anthracen.pdf | 845.42 kB | Adobe PDF | View/Open |
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