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Upgrading ketone synthesis direct from carboxylic acids and organohalides

The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling...

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Autores principales: Ruzi, Rehanguli, Liu, Kai, Zhu, Chengjian, Xie, Jin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7334210/
https://www.ncbi.nlm.nih.gov/pubmed/32620758
http://dx.doi.org/10.1038/s41467-020-17224-2
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author Ruzi, Rehanguli
Liu, Kai
Zhu, Chengjian
Xie, Jin
author_facet Ruzi, Rehanguli
Liu, Kai
Zhu, Chengjian
Xie, Jin
author_sort Ruzi, Rehanguli
collection PubMed
description The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals.
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spelling pubmed-73342102020-07-09 Upgrading ketone synthesis direct from carboxylic acids and organohalides Ruzi, Rehanguli Liu, Kai Zhu, Chengjian Xie, Jin Nat Commun Article The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals. Nature Publishing Group UK 2020-07-03 /pmc/articles/PMC7334210/ /pubmed/32620758 http://dx.doi.org/10.1038/s41467-020-17224-2 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Ruzi, Rehanguli
Liu, Kai
Zhu, Chengjian
Xie, Jin
Upgrading ketone synthesis direct from carboxylic acids and organohalides
title Upgrading ketone synthesis direct from carboxylic acids and organohalides
title_full Upgrading ketone synthesis direct from carboxylic acids and organohalides
title_fullStr Upgrading ketone synthesis direct from carboxylic acids and organohalides
title_full_unstemmed Upgrading ketone synthesis direct from carboxylic acids and organohalides
title_short Upgrading ketone synthesis direct from carboxylic acids and organohalides
title_sort upgrading ketone synthesis direct from carboxylic acids and organohalides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7334210/
https://www.ncbi.nlm.nih.gov/pubmed/32620758
http://dx.doi.org/10.1038/s41467-020-17224-2
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