Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Sven Solyntjes; Beate Neumann; Hans-Georg Stammler; Nikolai Ignat'ev; Berthold Hoge

doi:10.1002/chem.201604914

Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses

Chemistry. 2017 Jan 31;23(7):1568-1575. doi: 10.1002/chem.201604914. Epub 2016 Dec 14.

Authors

Sven Solyntjes¹, Beate Neumann¹, Hans-Georg Stammler¹, Nikolai Ignat'ev², Berthold Hoge¹

Affiliations

¹ Centrum für Molekulare Materialien, Fakultät für Chemie, Anorganische Chemie, Universität Bielefeld, Universitätsstraße 25, 33615, Bielefeld, Germany.
² Consultant Merck KGaA, Frankfurter Straße 250, 64293, Darmstadt, Germany.

PMID: 27874993
DOI: 10.1002/chem.201604914

Abstract

Commercially available BiPh₃ was treated with perfluoroalkylphosphinic acids [for example, (C₂ F₅ )₂ P(O)OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type Ph_x Bi[R^F₂ PO₂ ]_3-x (x=0, 1, 2) (R^F =-C₂ F₅ , -C₄ F₉ ). The first bismuth(V) perfluoroalkylphosphinate, Ph₃ Bi[(C₂ F₅ )₂ PO₂ ]₂ , was synthesized from Ph₃ BiCl₂ and Ag[(C₂ F₅ )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.

Keywords: bismuth; catalysis; green chemistry; perfluoroalkylphosphinic acid.