Catalytic Reductive Ring Opening of Epoxides Enabled by Zirconocene and Photoredox Catalysis
Junichiro Yamaguchi shows the use of zirconocene and photoredox catalysis in ring-opening reactions.
The epoxide ring is a key structural motif frequently found in biologically active compounds, natural feedstocks, and various synthetic intermediates. Generally, epoxides act as electrophiles, but C–O bond homolysis furnishes a nucleophilic carbon radical that can subsequently undergo a variety of functionalizations. According to Professor Junichiro Yamaguchi from Waseda University (Tokyo, Japan) “The most common catalyst for transformations related to epoxide C–O bond homolysis is titanocene(III) which has been exclusively exploited over the past 30 years by synthetic chemists.” Intrigued by the higher oxophilicity of zirconium compared to titanium, Professor Yamaguchi’s group became interested in using zirconocene for the ring opening of epoxides.