Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions

Since the pioneering contribution of Corey and Chaykovsky in 1965, sulfoxonium and sulfonium ylides have proven to be versatile intermediates in organic synthesis. One of their important applications, though not yet throughly investigated, is their substitution of diazocarbonyl compounds as safer carbene precursors. This microreview provides an overview and recent applications of sulfoxonium and sulfonium ylides in inter- and intramolecular metal-catalyzed insertion reactions. It also plans to illustrate the promising synthetic utility of these stable carbene precursors in industry, mitigating potential safety problems generally encountered when the equivalent diazo compounds are employed. Moreover, it aims to inspire new contributions to this exciting growing area, especially in catalytic asymmetric reactions.