Tetrabutylammonium difluorotriphenylsilicate

Preparative Methods prepared by treatment of triphenylsilyl fluoride with tetrabutylammonium fluoride (TBAF), or by reaction of triphenylsilane with tetrabutylammonium hydrogen difluoride.  

Purification recrystallized from EtOAc or CH2Cl2/hexanes. 

Handling, Storage, and Precautions reagent is extremely sensitive to acid. 

In the reaction of the mesylate corresponding to 1, the product fluoride was obtained as a mixture of diastereomers due to some epimerization. TBAT has also been employed in reactions of 6-chloropurine nucleosides, to give the corresponding fluorinated 

Allylation Reactions. In 1996, Pilcher and DeShong described the use of TBAT for the in situ generation of carbanions from various functionalized silane precursors, especially allyl-silane (eqs 3 and 4).  

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A copper enolate is also regarded as an intermediate in a hetero-Diels-Alder-like sequence between a ketone and an analog of Danishefsky s diene, modified at silicon ii.e., (0Et)3 in place of Mes Scheme 1-12)J A fluoride-initiated (tetrabutylammonium difluorotriphenylsilicate [TBAT]) cleavage of the starting silyl enol ether leads to a nonracemically ligated (with Walphos) copper enolate, which condenses and then closes to the observed dihydropyranones in modest ee s. Noteworthy in this scheme is generation of the quaternary center. 

Lithium 2,2,6,6-tetramethylpiperidide Lowest unoccupied molecular orbital Multicomponent coupling reaction Al-Iodosuccinimide Tetrabutylammonium fluoride Tetrabutylammonium difluorotriphenylsilicate t-Butyldimethylsilyl Trifluoromethanesulfonic anhydride Trimethylsilyl... 

TMAF), tetrabutylammonium difluorotriphenylsilicate (TBAT) or the mixed salt 1 1 CsF-CsOH. Furthermore, the reaction can benefit from the use of ionic liquids as reaction media. Finally, a polymer-supported fluoride initiator has also been described, thus improving the ease of purification of the products. ... 

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