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Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond format...

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Detalles Bibliográficos
Autor principal: Zhou, Lei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8621615/
https://www.ncbi.nlm.nih.gov/pubmed/34834143
http://dx.doi.org/10.3390/molecules26227051
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author Zhou, Lei
author_facet Zhou, Lei
author_sort Zhou, Lei
collection PubMed
description The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided.
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spelling pubmed-86216152021-11-27 Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis Zhou, Lei Molecules Review The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided. MDPI 2021-11-22 /pmc/articles/PMC8621615/ /pubmed/34834143 http://dx.doi.org/10.3390/molecules26227051 Text en © 2021 by the author. 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
Zhou, Lei
Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title_full Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title_fullStr Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title_full_unstemmed Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title_short Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
title_sort recent advances in c-f bond cleavage enabled by visible light photoredox catalysis
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8621615/
https://www.ncbi.nlm.nih.gov/pubmed/34834143
http://dx.doi.org/10.3390/molecules26227051
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