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

Wei Ding, Chang Chin Ho, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1202-1206
Number of pages5
JournalOrganic letters
Volume21
Issue number4
DOIs
Publication statusPublished - 2019 Feb 15
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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