Issue 54, 2017

A model for C–F activation by electrophilic phosphonium cations

Abstract

The synthesis of the electrophilic phosphonium cation (EPC) salt [C10H6(CF3)PF(C6F5)2][B(C6F5)4] 4 was achieved via oxidation of phosphine [C10H6(CF3)P(C6F5)2] 2 with XeF2 to form phosphorane [C10H6(CF3)PF2(C6F5)2] 3 and subsequent fluoride ion abstraction. Structural and spectroscopic characterization of 4 provides evidence of an interaction between the CF3 functionality and the phosphonium centre. AIM and NBO analyses also support donation from a lone pair on a fluorine atom of the CF3 group to the P–F σ* orbital of the fluorophosphonium unit, consistent with previously proposed mechanisms for main group C–F bond activations.

Graphical abstract: A model for C–F activation by electrophilic phosphonium cations

Supplementary files

Article information

Article type
Communication
Submitted
25 May 2017
Accepted
12 Jun 2017
First published
12 Jun 2017

Chem. Commun., 2017,53, 7529-7532

A model for C–F activation by electrophilic phosphonium cations

I. Mallov, T. C. Johnstone, D. C. Burns and D. W. Stephan, Chem. Commun., 2017, 53, 7529 DOI: 10.1039/C7CC04057A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements