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

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

*この研究の対応する著者

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1762-1774
ページ数13
ジャーナルChem
8
6
DOI
出版ステータスPublished - 2022 6月 9

ASJC Scopus subject areas

  • 化学 (全般)
  • 生化学
  • 環境化学
  • 化学工学(全般)
  • 生化学、医学
  • 材料化学

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