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Cross-dehydrogenative coupling for the intermolecular C–O bond formation
The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311763/ https://www.ncbi.nlm.nih.gov/pubmed/25670997 http://dx.doi.org/10.3762/bjoc.11.13 |
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author | Krylov, Igor B Vil’, Vera A Terent’ev, Alexander O |
author_facet | Krylov, Igor B Vil’, Vera A Terent’ev, Alexander O |
author_sort | Krylov, Igor B |
collection | PubMed |
description | The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O(2)CR)(2) reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.). |
format | Online Article Text |
id | pubmed-4311763 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-43117632015-02-10 Cross-dehydrogenative coupling for the intermolecular C–O bond formation Krylov, Igor B Vil’, Vera A Terent’ev, Alexander O Beilstein J Org Chem Review The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O(2)CR)(2) reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.). Beilstein-Institut 2015-01-20 /pmc/articles/PMC4311763/ /pubmed/25670997 http://dx.doi.org/10.3762/bjoc.11.13 Text en Copyright © 2015, Krylov et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Review Krylov, Igor B Vil’, Vera A Terent’ev, Alexander O Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title | Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title_full | Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title_fullStr | Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title_full_unstemmed | Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title_short | Cross-dehydrogenative coupling for the intermolecular C–O bond formation |
title_sort | cross-dehydrogenative coupling for the intermolecular c–o bond formation |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311763/ https://www.ncbi.nlm.nih.gov/pubmed/25670997 http://dx.doi.org/10.3762/bjoc.11.13 |
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