Abstract
Abstract Fluoride-ion-mediated reaction of trimethylsilylacetylene with carbonyl compounds has been thoroughly studied. The products of addition to the CO bond were obtained in 15–66% yield, their subsequent silylation and addition to the second molecule of the carbonyl compound being observed. It has been found that terminal aryl and hetaryl acetylenes undergo silylation in a two-phase-system Me 3 SiCCH/CsF/18-crown-6 to afford aryl(hetaryl) trimethylsilylacetylenes with up to 100% yields. Combining these two reactions, a novel one-pot fluoride-ion-mediated method for the synthesis of 1-trimethylsiloxy-3-aryl(hetaryl)-2-propynes from trimethylsilylacetylene, terminal aryl or hetaryl acetylenes and carbonyl compounds has been elaborated.
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