Synlett 2007(2): 0339-0340  
DOI: 10.1055/s-2007-968020
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Tetrabutylammonium Triphenyldifluorosilicate (TBAT)

Alex Cayley*
University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK
e-Mail: a.cayley@ucl.ac.uk;
Further Information

Publication History

Publication Date:
24 January 2007 (online)

Introduction

Tetrabutylammonium triphenyldifluorosilicate (TBAT, 1) is a hypervalent silicate which acts as a potent source of fluoride ions (Figure 1). The reagent has been widely ­exploited in organic chemistry as a means of carrying out nucleophilic fluorination reactions, [1] activating organo­silanes as nucleophiles [2-7] as well as acting as a coupling reagent in palladium-catalysed reactions. [8-10]

Figure 1

TBAT (1) is readily soluble in organic solvents, not appreciably basic, non-hygroscopic and trivial to obtain in anhydrous form. It therefore presents numerous advantages over other fluoride sources such as metal fluoride salts and tetraalkylammonium fluorides (such as TBAF) which often cause problems associated with basicity and the presence of water. [11]

    References

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