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Catalysts 2017, 7(11), 328; doi:10.3390/catal7110328

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

Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Orgánica e Inorgánica, IUQOEM, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, E-33006 Oviedo, Spain
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Received: 19 October 2017 / Revised: 1 November 2017 / Accepted: 2 November 2017 / Published: 6 November 2017
(This article belongs to the Special Issue Homogeneous Catalysis and Mechanisms in Water and Biphasic Media)

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. View Full-Text
Keywords: aqueous catalysis; alkynes; carboxylic acids; alkynoic acids; hydrocarboxylation reactions; cycloisomerization reactions; enol esters; lactones; β-oxo esters aqueous catalysis; alkynes; carboxylic acids; alkynoic acids; hydrocarboxylation reactions; cycloisomerization reactions; enol esters; lactones; β-oxo esters
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Francos, J.; Cadierno, V. Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review. Catalysts 2017, 7, 328.

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