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20.5.12.1.2.5 Variation 5: Palladium-Catalyzed Carboxylation of Alk-1-ynes with Carbon Monoxide and Alcohols

DOI: 10.1055/sos-SD-020-01178

Evano, G.Science of Synthesis, (2007201262.

Many studies have been carried out on the palladium-catalyzed carboxylation of terminal alkynes with carbon monoxide and alcohols to give alk-2-ynoic acid esters. If none of the first carboxylation reactions reported in the 1960s and 1970s proceed without reducing the triple bond, pioneering and still highly competitive work by Tsuji et al. has shown that simple alkynyl esters can be prepared via an oxidative carboxylation procedure.[‌128‌] The reaction proceeds under 1 atmosphere of carbon monoxide at room temperature in an alcohol, using a catalytic amount of palladium(II) chloride and a stoichiometric amount of copper(II) chloride, acting as a reoxidant, in the presence of sodium acetate to afford alk-2-ynoates 39 in high yields (Scheme 16).

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