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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...

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Detalles Bibliográficos
Autores principales: Chen, Pu, Huang, Huawen, Tan, Qi, Ji, Xiaochen, Zhao, Feng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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