Redox‐Neutral Electrochemical <i>Cis</i> ‐Cyclopropanation of Alkenes With Sulfoxonium Ylides

Abstract

ABSTRACT Herein, we report an efficient metal‐free and redox‐neutral electrochemical strategy for the cis ‐selective cyclopropanation of less active alkenes with sulfoxonium ylides. This protocol circumvents the limitations of traditional methods, which are typically restricted to electron‐deficient alkenes, and provides access to thermodynamically less stable cis ‐cyclopropanes. Furthermore, the resulting cyclopropanes can be readily diverted to hydroalkylation products via controlled cathodic reductive ring‐opening. Mechanistic studies support a radical cation‐mediated stepwise cycloaddition pathway, wherein the cis ‐diastereoselectivity is established during the initial radical addition. This sustainable approach not only broadens the synthetic utility of sulfoxonium ylides but also represents a significant advance in green electrochemical synthesis.