Palladium-catalyzed cross-coupling of styrenes with aryl methyl ketones in ionic liquids: direct access to cyclopropanes

Abstract

The combined use of Pd(OAc)2 , Cu(OAc)2 , and dioxygen in molten tetrabutylammonium acetate (TBAA) promotes an unusual cyclopropanation reaction between aryl methyl ketones and styrenes. The process is a dehydrogenative cyclizing coupling that involves a twofold CH activation at the α-position of the ketone. The substrate scope highlights the flexibility of the catalyst; a reaction mechanism is also proposed.

Keywords: CH activation; copper; cyclopropanation; ionic liquids; palladium.