Redox Potential Controlled Selective Oxidation of Styrenes for Regio- And Stereoselective Crossed Intermolecular [2 + 2] Cycloaddition via Organophotoredox Catalysis

Kenta Tanaka, Yoshinori Iwama, Mami Kishimoto, Naoya Ohtsuka, Yujiro Hoshino, Kiyoshi Honda, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A redox potential controlled intermolecular [2 + 2] cross-cycloaddition has been developed in the presence of a thioxanthylium photoredox catalyst. Electron-rich styrenes such as β-bromostyrene (Ep/2 = +1.61 V vs SCE) were selectively oxidized by a thioxanthylium photoredox catalyst (E1/2 (C*/C•-) = +1.76 V vs SCE) to styryl radical cations and reacted with styrene (Ep/2 = +1.97 V vs SCE) to furnish polysubstituted cyclobutanes in high yields. The present reaction can be successfully applied to intermolecular [2 + 2] cross-cycloaddition of β-halogenostyrenes, which cannot be effectively achieved by the hitherto reported representative organophotoredox catalysts.

Original languageEnglish
Pages (from-to)5207-5211
Number of pages5
JournalOrganic Letters
Volume22
Issue number13
DOIs
Publication statusPublished - Jul 2 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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