Fluoroalkenyl, fluoroalkynyl and fluoroalkyl phosphines

A review of the methods available for the preparation of monodentate P(III) compounds containing fluoroalkenyl, fluoroalkynyl and fluoroalkyl groups is given. The synthesis, properties and coordination chemistry of some fluoroalkenyl- and fluoroalkynyl-containing phosphines derived from HFC-134a (CF3CH2F) and HFC-245fa (CF3CH2CH2F) is summarised. The development of the reaction between trimethylsilyl-containing phosphines and RfI which provides a general method by which bulky fluoroalkyl groups, such as i-C3F7, t-C4F9, c-C6F11, can be readily introduced into phosphorus(III) centres is reported. Together these methods provide a way of generating P(III) systems of the type R3−nP(Rf)n capable of possessing a wide range of steric and electronic properties.

Graphical abstractA review of the methods for the preparation of P(III) compounds containing directly bound fluoroalkenyl, fluoroalkynyl and fluoroalkyl groups is given. Recent advances in the synthesis of organofluoro-containing phosphines are reported, including a new high yielding route to bulky fluoroalkyl-containing phosphines.Figure optionsDownload full-size imageDownload as PowerPoint slide