Sulfoxonium Ylides as Carbene Precursors in Rhodium-Catalyzed Sommelet-Hauser Rearrangement for the Synthesis of S/Se-Containing Compounds

Rhodium-catalyzed Sommelet-Hauser rearrangement derived from & alpha;-thioesters/& alpha;-selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium-containing ortho-substituted aromatic compounds in medium to excellent yields (39 examples; up to 97 %). Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet-Hauser rearrangement reactions, which is superior to traditional diazo compounds. The present reaction has the advantages of mild condition, safety and broad substrate scope, which afford a unique method for the synthesis of sulfur/selenium-containing compounds with a tertiary carbon center. Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet-Hauser rearrangement reactions for the synthesis of sulfur/selenium-containing compounds. The present reaction highlights the advantages of mild condition and broad substrate scope.image