101230

Tetrabutylammonium difluorotriphenylstannate

TBAF-Sn

TBAF-Sn (Gingras' Reagent) (1) 1 is a white, crystalline, nucleophilic fluorinating agent with a melting point of 192-193°C. It is used as an anhydrous synthetic equivalent to Tetrabutylammonium Fluoride (TBAF). In contrast to TBAF, it is stable for years and non hygroscopic. Its solubility in organic solvents is remarkable: CH2Cl2, CHCl3, THF, acetone and most polar solvents.

The nucleophilicity and reactivity of TBAF-Sn represents a nice compromise between the common fluorinating agents CsF and TBAF. It has been used as a fluoride source for nucleophilic displacement reactions and cleavage of carbon silicon bonds. Pd-catalyzed arylations were also shown.

Applications: A. Fluorination: Gem-Difluorides and Gem-Monohalogeno Fluoro Compounds (2).

B. Fluorination: Nucleophilic Displacement of Halides (1).

C. Alkylations of Enolsilylethers (1).

D. Transfer of Aryl Groups in Pd-Catalyzed Couplings (3,4).

E. Other Applications with Carbohydrates (5) and Generation of Difluoroenoxysilanes.

References

(1)	Gingras, M. Tetrahedron Lett. 1991, 32, 7381-7384.
(2)	García, A., Martínez; Osío Barcine, J.; Rys, A. Z.; Subramanian, L. R. Synlett 1993, 8, 587-588. Ibid, Tetrahedron Lett. 1992, 33, 7787-7788.
(3)	Buffnoir, S.; Mestdagh, H.; Rolando, C. Electron. Conf. Trends Org. Chem. (CD-ROM) 1996, Meeting date 1995, paper 42, Royal Society of Chemistry, UK.
(4)	Martinez, A. Garcia; Barcina, J; Osio; Cerezo, A. de Frensno; Subramanian, L. R. Synlett 1994, 12, 1047-1048.
(5)	Lavaire, S.; Plantier-Royon, R.; Portella, C. Tetrahedron Asymmetry 1998, 9, 213-226.
(6)	Brigaud, T.; Doussot, P. Charles, P. J. Chem. Soc. Chem. Comm. 1994, 18, 2117-2118.