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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| Format: | Article |
| Language: | English |
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MDPI AG
2017-11-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/7/11/328 |
| _version_ | 1811291015227637760 |
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| author | Javier Francos Victorio Cadierno |
| author_facet | Javier Francos Victorio Cadierno |
| author_sort | Javier Francos |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T04:22:08Z |
| format | Article |
| id | doaj.art-6932165816804fe29f1e3da0bc1c4ee4 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-04-13T04:22:08Z |
| publishDate | 2017-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-6932165816804fe29f1e3da0bc1c4ee42022-12-22T03:02:40ZengMDPI AGCatalysts2073-43442017-11-0171132810.3390/catal7110328catal7110328Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A ReviewJavier Francos0Victorio Cadierno1Laboratorio 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, SpainLaboratorio 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, SpainThe 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.https://www.mdpi.com/2073-4344/7/11/328aqueous catalysisalkynescarboxylic acidsalkynoic acidshydrocarboxylation reactionscycloisomerization reactionsenol esterslactonesβ-oxo esters |
| spellingShingle | Javier Francos Victorio Cadierno Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review Catalysts aqueous catalysis alkynes carboxylic acids alkynoic acids hydrocarboxylation reactions cycloisomerization reactions enol esters lactones β-oxo esters |
| title | Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review |
| title_full | Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review |
| title_fullStr | Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review |
| title_full_unstemmed | Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review |
| title_short | Metal-Catalyzed Intra- and Intermolecular Addition of Carboxylic Acids to Alkynes in Aqueous Media: A Review |
| title_sort | metal catalyzed intra and intermolecular addition of carboxylic acids to alkynes in aqueous media a review |
| topic | aqueous catalysis alkynes carboxylic acids alkynoic acids hydrocarboxylation reactions cycloisomerization reactions enol esters lactones β-oxo esters |
| url | https://www.mdpi.com/2073-4344/7/11/328 |
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