Synthesis of Functionalized Sulfoxonium Ylides and Their Synthetic Applications

Sulfur ylides are an important class of compounds in organic chemistry, widely used as building blocks in total synthesis, materials chemistry, and pharmaceutical development¹. This present study describes the synthesis of new functionalized sulfoxonium ylides containing reactive groups with potential for preparing novel molecules, including nitrogen- and oxygen-containing heterocycles. This work began with the synthesis of the acid chloride from phenylglyoxylic acid, employing dichloromethyl methyl ether and affording quantitative yield. In the subsequent reaction, trimethylsulfoxonium iodide and a base afforded a new ylide (1) bearing an epoxide group, in yields up to 11%. Additionally, a second ylide (2) derived from epoxide ring opening was isolated in 8% yield not optimized. Studies of X–H insertion reactions (X = N, O) via metal–carbene intermediates are currently underway, aiming to apply these new ylides as a versatile and promising synthetic platform for accessing a wide variety of substituted heterocycles².