C-F Bond Activation by Silylium Cation/Phosphine Frustrated Lewis Pairs: Mono-Hydrodefluorination of PhCF3 , PhCF2 H and Ph2 CF2

Ian Mallov; Adam J Ruddy; Hui Zhu; Stefan Grimme; Douglas W Stephan

doi:10.1002/chem.201705276

C-F Bond Activation by Silylium Cation/Phosphine Frustrated Lewis Pairs: Mono-Hydrodefluorination of PhCF₃ , PhCF₂ H and Ph₂ CF₂

Chemistry. 2017 Dec 14;23(70):17692-17696. doi: 10.1002/chem.201705276. Epub 2017 Nov 30.

Authors

Ian Mallov¹, Adam J Ruddy¹, Hui Zhu², Stefan Grimme², Douglas W Stephan¹

Affiliations

¹ Department of Chemistry, University of Toronto, 80 St. George St, Toronto, Ontario, M5S 3H6, Canada.
² Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115, Bonn, Germany.

PMID: 29116666
DOI: 10.1002/chem.201705276

Abstract

Single defluorination of aryl polyfluoromethyl functionalities is achieved by both intra- and intermolecular silylium cation/phosphine Lewis pairs. Phosphine-captured aryl fluoromethyl cations are then treated with Brønsted base to complete the first mono-hydrodefluorinations of PhCF₃ , Ph₂ CF₂ , and PhCF₂ .

Keywords: CF bond activation; fluorination; fluorine; silicon; silylium cations.