Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles

Abstract

A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97% yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic trans-aminoselenation, and followed by an oxidative cis-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired N-vinyl azoles in up to 88% yield and > 20:1 Z/E ratio.