One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent

We report a one-pot,three-component synthesis of sulfidesby exploitinga sulfoxide reagent as a formal sulfur dication equivalent. Our protocolconsists of three simple chemical operations involving two Grignardreagents and trimethylsilyl chloride (TMSCl) to sequentially formsulfenate anions, sulfenate esters, and sulfides. We demonstrate awide range of Grignard reagents to be coupled, thereby allowing themodular, thiol-free synthesis of sulfides including dialkenyl andalkenyl-alkynyl sulfides.

Automated summary

We describe a method for the one-pot, three-component synthesis of sulfides using a sulfoxide reagent as a formal sulfur dication equivalent. This protocol involves three simple chemical operations with two Grignard reagents and trimethylsilyl chloride (TMSCl) to sequentially generate sulfenate anions, sulfenate esters, and sulfides. We demonstrate the versatility of this method by synthesizing a wide range of sulfides, including dialkenyl and alkenyl-alkynyl sulfides, without the need for thiols.