Issue 37, 2016

Electrophilic phosphonium cations (EPCs) with perchlorinated-aryl substituents: towards air-stable phosphorus-based Lewis acid catalysts

Abstract

A series of phosphines incorporating (C6Cl5) substituents, Ph2P(C6Cl5) 1, PhP(C6Cl5)22, P(C6Cl5)33 and (C6F5)P(C6Cl5)24 were prepared. In the case of 1, 2 and 4, these were converted to the corresponding aryl-difluorophosphoranes 5–7via reaction with XeF2, whereas reaction of 3 with XeF2 afforded only an inseparable mixture of products. The compounds 5–7 were converted to the fluorophosphonium cations 8–10, whereas the reaction of 3 with Selectfluor afforded (C6Cl5)2POF and (C6Cl5)2. The fluorophosphonium salts showed evidence of improved air stability as well as Lewis acid catalytic activity in hydrodefluorination, hydrosilylation, deoxygenation and dehydrocoupling chemistry.

Graphical abstract: Electrophilic phosphonium cations (EPCs) with perchlorinated-aryl substituents: towards air-stable phosphorus-based Lewis acid catalysts

Supplementary files

Article information

Article type
Paper
Submitted
07 apr 2016
Accepted
23 apr 2016
First published
26 apr 2016

Dalton Trans., 2016,45, 14651-14657

Electrophilic phosphonium cations (EPCs) with perchlorinated-aryl substituents: towards air-stable phosphorus-based Lewis acid catalysts

S. Postle, V. Podgorny and D. W. Stephan, Dalton Trans., 2016, 45, 14651 DOI: 10.1039/C6DT01339B

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