Aryl Sulfoxides from Allyl Sulfoxides via [2,3]-Sigmatropic Rearrangement and Domino Pd-Catalyzed Generation/Arylation of Sulfenate Anions

Allylic sulfoxides, via [2,3]-sigmatropic rearrangement and oxidative addition of the resulting allylic sulfenate esters to Pd(0), are found to be excellent precursors of sulfenate anions. This hitherto unknown reactivity is applied in a new Pd(0)-catalyzed domino sequence Involving sulfenate anion generation followed by arylation to afford aryl sulfoxides.