Nickel-Catalyzed Cross-Coupling Reaction of Aryl Sulfoxides with Arylzinc Reagents: When the Leaving Group is an Oxidant

Abstract

Nickel-catalyzed Negishi-type cross-coupling of aryl methyl sulfoxides with arylzinc reagents has been developed. By consuming the catalyst-oxidizing methanesulfenate anion through oxidative homocoupling of the arylzinc reagent, smooth catalyst turnover could be executed. Arylzinc reagents prepared from arylmagnesium bromide, zinc bromide, and lithium bromide were optimal to afford the products in good to high yields, while arylzinc reagents prepared through other procedures showed lower reactivities. The reactivity of aryl methyl sulfoxide was compared with that of typical aryl (pseudo)halides.