Lanthanide catalysts with tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide ponytails: recyclable Lewis acid catalysts in fluorous phases or as solids

Abstract

Lanthanide tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide complexes are shown to be immobilized and continuously recycled in fluorous phases or as solids. The lanthanide complexes are thus extremely efficient Lewis acid catalysts for carbon–carbon bond forming (CCF) reactions. The CCF reactions such as the Friedel–Crafts acylation, Diels–Alder, and Mukaiyama aldol reaction are effectively catalyzed by the lanthanide complexes by virtue of the highly electron-withdrawing effect of tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide ponytails without any hydrocarbon spacer.