Copper-Catalyzed -Arylation of Sulfoxonium Ylides Using Hypervalent Iodine Compounds

A Cu(I)-catalyzed synthesis of alpha-arylated sulfoxonium ylides has been achieved from mesitylene-derived diaryliodonium salts and alpha-carbonyl sulfoxonium ylides. The reaction is believed to proceed via an electrophilic Cu(III)-aryl intermediate that can be trapped upon nucleophilic attack of the sulfoxonium ylide precursor. The reaction was tolerant to both alpha-keto and alpha-ester-derived sulfoxonium ylides, to drug-derived ylide motifs and to electronically-diverse arenes, and enabled the direct synthesis of 32 alpha-aryl-sulfoxonium ylides in 42-85% yield. image