Catalytic reductive ring opening of epoxides enabled by zirconocene and photoredox catalysis

Kazuhiro Aida, Marina Hirao, Aiko Funabashi, Natsuhiko Sugimura, Eisuke Ota*, Junichiro Yamaguchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The reductive ring opening of epoxides is a powerful transformation to convert readily accessible epoxides into a diverse array of valuable alcohols, including pharmaceuticals, agrochemicals, and functional polymers. Although significant progress has been made, the established methods were limited to titanocene-catalyzed reactions. Herein, we report an unprecedented zirconocene-catalyzed ring opening of epoxide enabled by photoredox catalysis. Compared with the conventional ring-opening methods, the present protocol exhibited reverse regioselectivity to afford more substituted alcohols via putative less-stable radicals. This reaction is remarkably mild and smoothly cleaves C–O bonds in molecules with a variety of functional groups, including natural products. We believe that the finding that changing the metal center in metallocene influences the energy profile of ring opening is a significant advance and provides a new perspective in radical chemistry with group IV metals.

Original languageEnglish
Pages (from-to)1762-1774
Number of pages13
JournalChem
Volume8
Issue number6
DOIs
Publication statusPublished - 2022 Jun 9

Keywords

  • SDG3: Good health and well-being
  • SDG9: Industry innovation and infrastructure
  • epoxide
  • photoredox catalysis
  • reverse regioselectivity
  • ring opening
  • zirconocene

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

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