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A model for C–F activation by electrophilic phosphonium cations

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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

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Publication details

The article was received on 25 May 2017, accepted on 12 Jun 2017 and first published on 12 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC04057A
Citation: Chem. Commun., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7CC04057A

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