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A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an S(N)2-based photochemical catalytic mechan...

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Detalles Bibliográficos
Autores principales: Cuadros, Sara, Horwitz, Matthew A., Schweitzer-Chaput, Bertrand, Melchiorre, Paolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6553376/
https://www.ncbi.nlm.nih.gov/pubmed/31293731
http://dx.doi.org/10.1039/c9sc00833k
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author Cuadros, Sara
Horwitz, Matthew A.
Schweitzer-Chaput, Bertrand
Melchiorre, Paolo
author_facet Cuadros, Sara
Horwitz, Matthew A.
Schweitzer-Chaput, Bertrand
Melchiorre, Paolo
author_sort Cuadros, Sara
collection PubMed
description We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an S(N)2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.
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spelling pubmed-65533762019-07-10 A visible-light mediated three-component radical process using dithiocarbamate anion catalysis Cuadros, Sara Horwitz, Matthew A. Schweitzer-Chaput, Bertrand Melchiorre, Paolo Chem Sci Chemistry We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an S(N)2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products. Royal Society of Chemistry 2019-04-30 /pmc/articles/PMC6553376/ /pubmed/31293731 http://dx.doi.org/10.1039/c9sc00833k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Cuadros, Sara
Horwitz, Matthew A.
Schweitzer-Chaput, Bertrand
Melchiorre, Paolo
A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title_full A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title_fullStr A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title_full_unstemmed A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title_short A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
title_sort visible-light mediated three-component radical process using dithiocarbamate anion catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6553376/
https://www.ncbi.nlm.nih.gov/pubmed/31293731
http://dx.doi.org/10.1039/c9sc00833k
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