| Journal Title /掲載ジャーナル名 |
Chem |
| Publication Year and Month /掲載年月 |
April, 2022 |
| Paper Title /論文タイトル |
Catalytic Reductive Ring Opening of Epoxides Enabled by Zirconocene and Photoredox Catalysis |
| DOI /論文DOI |
10.1016/j.chempr.2022.04.010 |
| Author of Waseda University /本学の著者 |
AIDA,Kazuhiro(Student, Faculty of Science and Engineering, School of Advanced Science and Engineering):First Author
YAMAGUCHI, Junichiro (Professor, Faculty of Science and Engineering, School of Advanced Science and Engineering):Corresponding Author |
| Related Websites /関連Web |
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| Abstract /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. |
