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Tetrabutylammonium Fluoride (TBAF)-Catalyzed Addition of Substituted Trialkylsilylalkynes to Aldehydes, Ketones, and Trifluoromethyl Ketones

Venkat Reddy Chintareddy, Kuldeep Wadhwa and John G. Verkade*

*Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, United States, Email: jverkadeiastate.edu

V. R. Chintareddy, H. Wadhwa, J. G. Verkade, J. Org. Chem., 2011, 76, 4482-4488.

DOI: 10.1021/jo200314g (free Supporting Information)


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Abstract

Tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for a mild and operationally simple addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF at room temperature. The reaction conditions tolerate various aryl functional groups, such as chloro, trifluoromethyl, bromo, and fluoro groups. Product yields are generally better than or comparable to those in the literature.

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Key Words

propargylic alcohols


ID: J42-Y2011-1550