title: Tetrabutylammonium fluoride (TBAF)-catalyzed addition of substituted trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones.
abstract: Herein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and operationally simple, and a variety of aryl functional groups, such as chloro, trifluoromethyl, bromo, and fluoro groups, are tolerated. Impressively, using our protocol, useful CF(3)-bearing tertiary propargylic alcohols can be synthesized. Product yields are generally better than or comparable to those in the literature. 1-Phenyl-2-trimethylsilyl acetylene, trimethyl ((4-(trifluoromethyl)phenyl)ethynyl)silane, 1-trimethylsilyl-1-hexyne, and trimethyl(thiophen-3-ylethynyl)silane underwent clean conversion to their corresponding propargylic alcohols as products under our conditions. Heterocyclic carbonyl compounds, such as furan-3-carboxaldehyde, thiophene-3-carboxaldehyde, and 2-pyridyl ketone, gave good yields of propargylic alcohols.
authors.affiliation: Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, United States.
authors.forename: Venkat Reddy
authors.initials: VR
authors.lastname: Chintareddy
authors.forename: Kuldeep
authors.initials: K
authors.lastname: Wadhwa
authors.forename: John G
authors.initials: JG
authors.lastname: Verkade