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DOI: 10.1055/sos-SD-207-00308

Chartoire, A.; Nolan, S. P.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131520.

Alkynylsilanes 27 can be coupled with propargyl chlorides 28 in the presence of a catalytic amount of copper(I) iodide and a fluoride source to yield the corresponding 1,4-skipped diynes 29 in good yields (Scheme 8).[‌34‌] The reaction can be promoted by either cesium fluoride or tetrabutylammonium fluoride and requires a polar solvent such as 1,3-dimethylimidazolidin-2-one at 80 °C. It is noteworthy that the reaction does not proceed if the substrate bears a nitrogen atom (pyridine or amine). A similar procedure has also been reported allowing the alkynylation of allyl halides in the presence of potassium fluoride and copper(I) iodide in dimethylformamide.[‌35‌]

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