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One-Pot Enol Silane Formation-Alkylation of Ketones with Propargyl Carboxylates Promoted by Trimethylsilyl Trifluoromethanesulfonate

C. Wade Downey*, Danielle N. Confair, Yiqi Liu, Elizabeth D. Heafner

*Gottwald Center for the Sciences, University of Richmond, 28 Westhampton Way, Richmond, Virginia 23173, United States, Email: wdowneyrichmond.edu

C. Wade Downey, D. N. Confair, Y. Liu, E. D. Heafner, J. Org. Chem., 2018, 83, 12931-12938.

DOI: 10.1021/acs.joc.8b01997 (free Supporting Information)


Abstract

Ketones readily undergo conversion to enol silanes in the presence of a trialkylamine base and trimethylsilyl trifluoromethanesulfonate and add to propargyl cations, which are generated in situ through a TMSOTf-promoted ionization of propargyl carboxylates. A range of enol silane precursors and propargyl carboxylates reacts efficiently to provide β-alkynyl ketones in good yields.


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Key Words

carbonyl compounds, propargylation


ID: J42-Y2018