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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...

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Autores principales: Shetgaonkar, Samata E., Raju, Aleena, China, Hideyasu, Takenaga, Naoko, Dohi, Toshifumi, Singh, Fateh V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
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.
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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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