Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions

Kenta Tanaka, Mami Kishimoto, Yuta Tanaka, Yusuke Kamiyama, Yosuke Asada, Mayumi Sukekawa, Naoya Ohtsuka, Toshiyasu Suzuki, Norie Momiyama, Kiyoshi Honda, Yujiro Hoshino

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E1/2(C*/C•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (Ep/2= 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.

Original languageEnglish
Pages (from-to)3319-3328
Number of pages10
JournalJournal of Organic Chemistry
Volume87
Issue number5
DOIs
Publication statusPublished - Mar 4 2022
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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