Base-catalyzed addition of silylacetylenes to ketones: a route to protected tertiary propargyl alcohols

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Abstract

The base-catalyzed addition of alkynylsilanes to ketone derivatives enables the formation of various silyl-protected propargylic alcohols. Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst and permits the functionalization of a variety of derivatives, including pharmaceuticals and biorelevant compounds. Overall, the presented system complements classical routes to protected tertiary propargylic alcohols that mainly rely on stoichiometric processes or fluoride-mediated reactions.

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Kuciński, K., Łuczak, A., Mankouski, A., & Hreczycho, G. (2023). Base-catalyzed addition of silylacetylenes to ketones: a route to protected tertiary propargyl alcohols. Organic Chemistry Frontiers, 10(11), 2752–2759. https://doi.org/10.1039/d3qo00579h

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