Synthesis 2019; 51(23): 4473-4486
DOI: 10.1055/s-0039-1690621
paper
© Georg Thieme Verlag Stuttgart · New York

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

Saeesh R. Mangaonkar
,
Financial support by the DST New Delhi (Grant No.: SB/FT/CS-068/2014) is gratefully acknowledged.
Further Information

Publication History

Received: 24 June 2019

Accepted after revision: 07 August 2019

Publication Date:
05 September 2019 (online)


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.

Supporting Information

 
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