Highly efficient heterogeneous copper-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with aryl halides leading to polyfluorobiaryls

Abstract

The heterogeneous decarboxylative cross-coupling reaction of potassium polyfluorobenzoates with aryl iodides and bromides was achieved in diglyme or DMAc at 130 or 160 °C in the presence of 10-20 mol% of a 1,10-phenanthroline-functionalized MCM-41-immobilized copper(i) complex, [MCM-41-Phen-CuI], yielding a variety of polyfluorobiaryls in good to excellent yields. This heterogeneous copper(i) complex could easily be prepared via a simple procedure from commercially readily available and inexpensive reagents, exhibited the same catalytic activity as the homogeneous CuI/Phen system, and was recovered by filtration of the reaction solution and recycled at least 8 times without significant loss of catalytic activity.