Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes

Abstract

A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 mol% PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.

Key words

epoxidation reaction - β-cyanostyrene - β-cyanoepoxide - iodobenzene - trifluoroacetic acid - Oxone

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