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Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic metho...

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Autores principales: Azizollahi, Hamid, García-López, José-Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7764206/
https://www.ncbi.nlm.nih.gov/pubmed/33322116
http://dx.doi.org/10.3390/molecules25245900
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author Azizollahi, Hamid
García-López, José-Antonio
author_facet Azizollahi, Hamid
García-López, José-Antonio
author_sort Azizollahi, Hamid
collection PubMed
description The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.
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spelling pubmed-77642062020-12-27 Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage Azizollahi, Hamid García-López, José-Antonio Molecules Review The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds. MDPI 2020-12-13 /pmc/articles/PMC7764206/ /pubmed/33322116 http://dx.doi.org/10.3390/molecules25245900 Text en © 2020 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Azizollahi, Hamid
García-López, José-Antonio
Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title_full Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title_fullStr Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title_full_unstemmed Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title_short Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage
title_sort recent advances on synthetic methodology merging c–h functionalization and c–c cleavage
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7764206/
https://www.ncbi.nlm.nih.gov/pubmed/33322116
http://dx.doi.org/10.3390/molecules25245900
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