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43.4.1.2 Method 2: Copper-Mediated Reactions

DOI: 10.1055/sos-SD-043-00183

Burmester, C.; Haß, O.; Faust, R.Science of Synthesis, (200843235.

A number of studies have been directed toward the synthesis of enynes and allenynes by reactions with catalytic or stoichiometric amounts of copper, as an alternative to the more frequently used palladium reagents (see Section 43.4.1.1). The reactions proceed either via alkynyl- or vinylcopper species, both often prepared in situ. Vinylcopper intermediates can be obtained by the deprotonation of alkenes followed by the addition of copper salts, or by transmetalation reactions starting from other vinyl metal intermediates. Vinylcopper species are then transformed in cross-coupling reactions with ethynyl halides to form the enyne. Alkynylcopper reagents, on the other hand, are commonly prepared from terminal alkynes in the presence of catalytic amounts of copper salts and a suitable base. Cross coupling then takes place with vinyl halides. Often, accessibility and handling convenience of the reagents make this version the method of choice.


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