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Synlett 2012(3): 480-481  
DOI: 10.1055/s-0031-1290134
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© Georg Thieme Verlag Stuttgart ˙ New York

Diphenylvinylsulfonium Triflate

Sven P. Fritz*
School of Chemistry, University of Bristol, Cantock’s Close, ­Bristol, BS8 1TS, UK
e-Mail: sven.fritz@bristol.ac.uk;
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Publication History

Publication Date:
25 January 2012 (online)

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Introduction

Diphenylvinylsulfonium triflate (1) is a pale, yellow, stable and free-flowing oil. It can easily be prepared from its commercially available precursor diphenylbromoethylsulfonium triflate (2, Scheme  [¹] ). Alternatively, it is also possible to generate vinylsulfonium salt 1 in situ from bromide 2.

Nucleophiles readily undergo conjugate addition to vinylsulfonium salts to form sulfur ylide intermediates, which can undergo a range of further transformations.

Extensive use in epoxidation, aziridination and other annulation reactions has shown the wide applicability of vinylsulfonium salts as two-carbon bridges.

Scheme 1 Preparation of diphenylvinylsulfonium triflate (1).

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