Subscribe to RSS
DOI: 10.1055/s-2007-968020
Tetrabutylammonium Triphenyldifluorosilicate (TBAT)
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]
- 1
Pilcher AS.Ammon HL.DeShong P. J. Am. Chem. Soc. 1995, 117: 5166 - 2
Pilcher AS.DeShong P. J. Org. Chem. 1996, 61: 6901 - 3
Friestad GK.Ding H. Angew. Chem. Int. Ed. 2001, 40: 4491 - 4
Friestad GK.Korapala CS.Ding H. J. Org. Chem. 2006, 71: 281 - 5
Biddle MM.Reich HJ. J. Org. Chem. 2006, 71: 4031 - 6
Furman B.Dziedzic M. Tetrahedron Lett. 2003, 44: 6629 - 7
Ley SV.Dixon DJ.Guy RT.Rodriguez F.Sheppard T. Org. Biomol. Chem. 2005, 3: 4095 - 8
Brescia MR.DeShong P. J. Org. Chem. 1998, 63: 3156 - 9
Mowery ME.DeShong P. J. Org. Chem. 1999, 64: 1684 - 10
Mowery ME.DeShong P. J. Org. Chem. 1999, 64: 3266 - 11
Cox DP.Terpinsky J.Lawrynowicz W. J. Org. Chem. 1984, 49: 3216 - 12
Handy CJ.Lam YF.DeShong P. J. Org. Chem. 2000, 65: 3542