Direct perfluoroalkylation of aromatic and heteroaromatic compounds with perfluoroalkanesulfonyl chlorides catalysed by a ruthenium(II) phosphine complex

Abstract

The perfluoroalkylation of aromatic and heteroaromatic compounds by perfluoroalkanesulfonyl chlorides 1 has been investigated in the presence of a ruthenium(II) phosphine complex. The reaction of compounds 1 with substituted benzenes or thiophenes proceeded smoothly with extrusion of sulfur dioxide at 120 °C to give corresponding perfluoroalkylated compounds in good yield. No expected perfluoroalkylated product was obtained in the reaction of compounds 1 with pyrrole; however, 1-trimethylsilyl- and 1-triisopropylsilyl-pyrrole were regioselectively perfluoroalkylated at their 2- and 3-position, respectively.