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Abstract
The metal-catalyzed addition of carboxylic acids to alkynes is a very effective tool for the synthesis of carboxylate-functionalized olefinic compounds in an atom-economical manner. Thus, a large variety of synthetically useful lactones and enol-esters can be accessed through the intra- or intermolecular versions of this process. In order to reduce the environmental impact of these reactions, considerable efforts have been devoted in recent years to the development of catalytic systems able to operate in aqueous media, which represent a real challenge taking into account the tendency of alkynes to undergo hydration in the presence of transition metals. Despite this, different Pd, Pt, Au, Cu and Ru catalysts capable of promoting the intra- and intermolecular addition of carboxylic acids to alkynes in a selective manner in aqueous environments have appeared in the literature. In this review article, an overview of this chemistry is provided. The synthesis of β-oxo esters by catalytic addition of carboxylic acids to terminal propargylic alcohols in water is also discussed.
Highlights
The transition metal-catalyzed heterofunctionalization of alkynes by addition of nucleophiles to the C≡C bond has emerged in recent years as a versatile synthetic tool in organic chemistry [1,2,3]
The addition of carboxylic acids to alkynes, reaction referred in the literature as hydro-oxycarbonylation or hydrocarboxylation of alkynes, represents a straightforward way to obtain different types of olefinic esters with atom economy [4,5,6]
A large variety of transition metal complexes have been used to catalyze these reactions through the π-activation of the carbon-carbon triple bond of the alkynoic acid, the regioselectivity
Summary
The transition metal-catalyzed heterofunctionalization of alkynes by addition of nucleophiles to the C≡C bond has emerged in recent years as a versatile synthetic tool in organic chemistry [1,2,3]. C≡C bonds is At commonly disfavours their coordination the metal catalyst At this it should be noted that a reduced should beof thatvs.a terminal reduced ofisinternal vs. C≡Ccase is commonly observed innoted the cyclization reactions alkynoic acids, in this problem is not so reactivity internal. Carboxylic acids to terminal propargylic alcohols in water is discussed
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