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Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents
Transition metal-catalyzed direct oxidative coupling reactions via C–H bond activation have emerged as a straightforward strategy for the construction of complex molecules in organic synthesis. The direct transformation of C–H bonds into carbon–carbon and carbon–heteroatom bonds renders the requirem...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9283985/ https://www.ncbi.nlm.nih.gov/pubmed/35844643 http://dx.doi.org/10.3389/fchem.2022.909250 |
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author | Shetgaonkar, Samata E. Raju, Aleena China, Hideyasu Takenaga, Naoko Dohi, Toshifumi Singh, Fateh V. |
author_facet | Shetgaonkar, Samata E. Raju, Aleena China, Hideyasu Takenaga, Naoko Dohi, Toshifumi Singh, Fateh V. |
author_sort | Shetgaonkar, Samata E. |
collection | PubMed |
description | Transition metal-catalyzed direct oxidative coupling reactions via C–H bond activation have emerged as a straightforward strategy for the construction of complex molecules in organic synthesis. The direct transformation of C–H bonds into carbon–carbon and carbon–heteroatom bonds renders the requirement of prefunctionalization of starting materials and, therefore, represents a more efficient alternative to the traditional cross-coupling reactions. The key to the unprecedented progress made in this area has been the identification of an appropriate oxidant that facilitates oxidation and provides heteroatom ligands at the metal center. In this context, hypervalent iodine compounds have evolved as mainstream reagents particularly because of their excellent oxidizing nature, high electrophilicity, and versatile reactivity. They are environmentally benign reagents, stable, non-toxic, and relatively cheaper than inorganic oxidants. For many years, palladium catalysis has dominated these oxidative coupling reactions, but eventually, other transition metal catalysts such as gold, copper, platinum, iron, etc. were found to be promising alternate catalysts for facilitating such reactions. This review article critically summarizes the recent developments in non-palladium-catalyzed oxidative coupling reactions mediated by hypervalent iodine (III) reagents with significant emphasis on understanding the mechanistic aspects in detail. |
format | Online Article Text |
id | pubmed-9283985 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-92839852022-07-16 Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents Shetgaonkar, Samata E. Raju, Aleena China, Hideyasu Takenaga, Naoko Dohi, Toshifumi Singh, Fateh V. Front Chem Chemistry Transition metal-catalyzed direct oxidative coupling reactions via C–H bond activation have emerged as a straightforward strategy for the construction of complex molecules in organic synthesis. The direct transformation of C–H bonds into carbon–carbon and carbon–heteroatom bonds renders the requirement of prefunctionalization of starting materials and, therefore, represents a more efficient alternative to the traditional cross-coupling reactions. The key to the unprecedented progress made in this area has been the identification of an appropriate oxidant that facilitates oxidation and provides heteroatom ligands at the metal center. In this context, hypervalent iodine compounds have evolved as mainstream reagents particularly because of their excellent oxidizing nature, high electrophilicity, and versatile reactivity. They are environmentally benign reagents, stable, non-toxic, and relatively cheaper than inorganic oxidants. For many years, palladium catalysis has dominated these oxidative coupling reactions, but eventually, other transition metal catalysts such as gold, copper, platinum, iron, etc. were found to be promising alternate catalysts for facilitating such reactions. This review article critically summarizes the recent developments in non-palladium-catalyzed oxidative coupling reactions mediated by hypervalent iodine (III) reagents with significant emphasis on understanding the mechanistic aspects in detail. Frontiers Media S.A. 2022-07-01 /pmc/articles/PMC9283985/ /pubmed/35844643 http://dx.doi.org/10.3389/fchem.2022.909250 Text en Copyright © 2022 Shetgaonkar, Raju, China, Takenaga, Dohi and Singh. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Shetgaonkar, Samata E. Raju, Aleena China, Hideyasu Takenaga, Naoko Dohi, Toshifumi Singh, Fateh V. Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title | Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title_full | Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title_fullStr | Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title_full_unstemmed | Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title_short | Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents |
title_sort | non-palladium-catalyzed oxidative coupling reactions using hypervalent iodine reagents |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9283985/ https://www.ncbi.nlm.nih.gov/pubmed/35844643 http://dx.doi.org/10.3389/fchem.2022.909250 |
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