The first heterogeneous carbonylative Stille coupling of organostannanes with aryl iodides catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex

Abstract

The first heterogeneous carbonylative Stille coupling reaction of organostannanes with aryl iodides under an atmospheric pressure of carbon monoxide has been achieved in DMF at 80 °C in the presence of a catalytic amount of an MCM-41-supported bidentate phosphine palladium(0) complex [MCM-41-2P-Pd(0)], yielding a variety of unsymmetrical ketones in good to high yields. This polymeric palladium catalyst exhibited higher activity and selectivity than PdCl₂(PPh₃)₂ and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of carbon monoxide under pressure, but also solves the basic problem of palladium catalyst recovery and reuse.