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Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters
The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-center...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10058904/ https://www.ncbi.nlm.nih.gov/pubmed/36985637 http://dx.doi.org/10.3390/molecules28062667 |
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author | Chen, Pu Huang, Huawen Tan, Qi Ji, Xiaochen Zhao, Feng |
author_facet | Chen, Pu Huang, Huawen Tan, Qi Ji, Xiaochen Zhao, Feng |
author_sort | Chen, Pu |
collection | PubMed |
description | The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N–O bond and C–C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives. These contents were systematically classified according to different reaction types. In this review, the free radical reactions involving acyl oxime esters and cyclic ketoxime esters after 2021 were included, with emphasis on the substrate scope and reaction mechanism. |
format | Online Article Text |
id | pubmed-10058904 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100589042023-03-30 Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters Chen, Pu Huang, Huawen Tan, Qi Ji, Xiaochen Zhao, Feng Molecules Review The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N–O bond and C–C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives. These contents were systematically classified according to different reaction types. In this review, the free radical reactions involving acyl oxime esters and cyclic ketoxime esters after 2021 were included, with emphasis on the substrate scope and reaction mechanism. MDPI 2023-03-15 /pmc/articles/PMC10058904/ /pubmed/36985637 http://dx.doi.org/10.3390/molecules28062667 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Review Chen, Pu Huang, Huawen Tan, Qi Ji, Xiaochen Zhao, Feng Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title | Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title_full | Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title_fullStr | Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title_full_unstemmed | Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title_short | Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters |
title_sort | recent advances in molecule synthesis involving c-c bond cleavage of ketoxime esters |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10058904/ https://www.ncbi.nlm.nih.gov/pubmed/36985637 http://dx.doi.org/10.3390/molecules28062667 |
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