Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

Abstract

An efficient method for the synthesis of alkyl indium reagents by means of an indium(III) or lead(II) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R₃In₂X₃, the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX₂) and a dialkyl indium halide (R₂InX) (both of them presumably exist as dimers).