Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Commercially available BiPh3 was treated with perfluoroalkylphosphinic acids [for example, (C2F5)(2)P(O) OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type PhxBi[(R2PO2)-P-F](3-x) (x= 0, 1, 2) (R-F =-C2F5, -C-4 F-9). The first bismuth(V) perfluoroalkylphosphinate, Ph3Bi[(C2F5)(2)PO2](2), was synthesized from Ph3BiCl2 and Ag[(C2F5)(2)PO2]. Examples for the successful application of the catalytically active bismuth(III) and bismuth(V) phosphinates in carbon-carbon bond forming reactions, such as Friedel-Crafts acylation and alkylation, Diels-Alder, Strecker and Mannich reaction, are presented.