Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review
Cascade reactions provide a straightforward access to many valuable compounds and reduce considerably the number of steps of a synthetic sequence. Among the domino and multicomponent processes that involve alkynes, the cascade reaction between alkynoic acids and C-, N-, O- and S-aminonucleophiles st...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/13/3/495 |
| _version_ | 1797612924241444864 |
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| author | María Teresa Herrero Jokin Díaz de Sarralde Nerea Conde Aitor Herrán Garazi Urgoitia Raul SanMartin |
| author_facet | María Teresa Herrero Jokin Díaz de Sarralde Nerea Conde Aitor Herrán Garazi Urgoitia Raul SanMartin |
| author_sort | María Teresa Herrero |
| collection | DOAJ |
| description | Cascade reactions provide a straightforward access to many valuable compounds and reduce considerably the number of steps of a synthetic sequence. Among the domino and multicomponent processes that involve alkynes, the cascade reaction between alkynoic acids and C-, N-, O- and S-aminonucleophiles stands out as a particularly powerful tool for the one-pot construction of libraries of nitrogen-containing heterocyclic compounds with scaffold diversity and molecular complexity. This reaction, based on an initial metal-catalyzed cycloisomerization that generates an alkylidene lactone intermediate, was originally catalyzed by gold(I) catalysts, along with silver salts or Brönsted acid additives, but other alternative metal catalysts have emerged in the last decade as well as different reaction media. This review examines the existing literature on the topic of metal-catalyzed cascade reactions of acetylenic acids and dinucleophiles and discusses aspects concerning substrate/catalyst ratio for every catalyst system, nature of the aminonucleophile involved and substrate scope. In addition, alternative solvents are also considered, and an insight into the pathway of the reaction and possible intermediates is also provided. |
| first_indexed | 2024-03-11T06:48:44Z |
| format | Article |
| id | doaj.art-89756cf93882426888d3392dbb0f9195 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T06:48:44Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-89756cf93882426888d3392dbb0f91952023-11-17T10:10:13ZengMDPI AGCatalysts2073-43442023-02-0113349510.3390/catal13030495Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A ReviewMaría Teresa Herrero0Jokin Díaz de Sarralde1Nerea Conde2Aitor Herrán3Garazi Urgoitia4Raul SanMartin5Department of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainDepartment of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainDepartment of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainDepartment of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainDepartment of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainDepartment of Organic and Inorganic Chemistry, Faculty of Science and Technology, University of the Basque Country (UPV/EHU), Sarriena Auzoa, z/g, 48940 Leioa, SpainCascade reactions provide a straightforward access to many valuable compounds and reduce considerably the number of steps of a synthetic sequence. Among the domino and multicomponent processes that involve alkynes, the cascade reaction between alkynoic acids and C-, N-, O- and S-aminonucleophiles stands out as a particularly powerful tool for the one-pot construction of libraries of nitrogen-containing heterocyclic compounds with scaffold diversity and molecular complexity. This reaction, based on an initial metal-catalyzed cycloisomerization that generates an alkylidene lactone intermediate, was originally catalyzed by gold(I) catalysts, along with silver salts or Brönsted acid additives, but other alternative metal catalysts have emerged in the last decade as well as different reaction media. This review examines the existing literature on the topic of metal-catalyzed cascade reactions of acetylenic acids and dinucleophiles and discusses aspects concerning substrate/catalyst ratio for every catalyst system, nature of the aminonucleophile involved and substrate scope. In addition, alternative solvents are also considered, and an insight into the pathway of the reaction and possible intermediates is also provided.https://www.mdpi.com/2073-4344/13/3/495cascade reactionsdomino processesmetal catalystscycloisomerization |
| spellingShingle | María Teresa Herrero Jokin Díaz de Sarralde Nerea Conde Aitor Herrán Garazi Urgoitia Raul SanMartin Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review Catalysts cascade reactions domino processes metal catalysts cycloisomerization |
| title | Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review |
| title_full | Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review |
| title_fullStr | Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review |
| title_full_unstemmed | Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review |
| title_short | Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles: A Review |
| title_sort | metal catalyzed cascade reactions between alkynoic acids and dinucleophiles a review |
| topic | cascade reactions domino processes metal catalysts cycloisomerization |
| url | https://www.mdpi.com/2073-4344/13/3/495 |
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