Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds > Alkylations
Propargylations
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Recent Literature
A ruthenium-catalyzed propargylic alkylation of propargylic alcohols with
various ketones provides the corresponding γ-keto acetylene products in
high yields under mild and neutral reaction conditions with complete
regioselectivities.
Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura, M. Hidai, J. Am. Chem. Soc., 2001,
123, 3393-3394.
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.
C. Wade Downey, D. N. Confair, Y. Liu, E. D. Heafner, J. Org. Chem., 2018, 83,
12931-12938.