Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review

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 intermole...

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Bibliographic Details
Published in:Catalysts 2017-11, Vol.7 (11), p.328
Main Authors: Francos, Javier, Cadierno, Victorio
Format: Article
Language:English
Subjects:
Acids
Alcohols
Alkynes
alkynoic acids
aqueous catalysis
Aqueous environments
Carboxylic acids
Catalysis
Catalysts
Chemical reactions
Chemical synthesis
Copper
cycloisomerization reactions
enol esters
Environmental impact
Esters
Gold
hydrocarboxylation reactions
Lactones
Literature reviews
Palladium
Platinum
Transition metals
β-oxo esters
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Summary: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.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal7110328