title: Utilization of Tetrabutylammonium Triphenyldifluorosilicate as a Fluoride Source for Silicon-Carbon Bond Cleavage.
abstract: Tetrabutylammonium triphenyldifluorosilicate (TBAT) can be employed as a fluoride source to cleave silicon-carbon bonds thus generating in situ carbanions that coupled with a variety of electrophiles, including aldehydes and ketones, in moderate to high yields. Among the examples reported is the first instance of fluoride-induced intermolecular coupling between allyltrimethylsilane and imine derivatives. Also, of particular note is the TBAT-initiated coupling of primary alkyl halides with allyltrimethylsilane. TBAT is an easily handled crystalline solid that has several advantages over tetrabutylammonium fluoride (TBAF) as a fluoride source; it is anhydrous, nonhygroscopic, soluble in most commonly used organic solvents, and less basic than TBAF.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742.
authors.forename: Anthony S.
authors.initials: AS
authors.lastname: Pilcher
authors.forename: Philip
authors.initials: P
authors.lastname: DeShong