Issue 84, 2016
From the journal:

Chemical Communications

S(vi) Lewis acids: fluorosulfoxonium cations†

Fu An Tsao,‡a   Alexander E. Waked,‡a   Levy Cao,a   Jordan Hofmann,a   Lei Liu,b   Stefan Grimmeb  and  Douglas W. Stephan*a  

* Corresponding authors

a Department of Chemistry, University of Toronto, 80 St. George St, Toronto, Ontario, Canada
E-mail: dstephan@chem.utoronto.ca

b Mulliken Center for Theoretical Chemistry, Institut fuer Physikalische und Theoretische Chemie, Universitaet Bonn, Beringstrasse 4, D-53115 Bonn, Germany

Abstract

Avenues to S-based Lewis acids were developed via the oxidation of aryl-sulfoxides with XeF2, giving difluorodiarylsulfoxides which react via fluoride abstraction to afford Lewis acidic fluorosulfoxonium cations; this acidity is derived from the S–F σ* orbital and has been probed both experimentally and computationally.

Graphical abstract: S(vi) Lewis acids: fluorosulfoxonium cations

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Article information

DOI
https://doi.org/10.1039/C6CC06929K
Article type
Communication
Submitted
23 Aug 2016
Accepted
09 Sep 2016
First published
09 Sep 2016

Chem. Commun., 2016,52, 12418-12421

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S(VI) Lewis acids: fluorosulfoxonium cations

F. A. Tsao, A. E. Waked, L. Cao, J. Hofmann, L. Liu, S. Grimme and D. W. Stephan, Chem. Commun., 2016, 52, 12418 DOI: 10.1039/C6CC06929K

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