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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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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. |
format | Online Article Text |
id | pubmed-6553376 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
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title_fullStr | A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
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title_full_unstemmed | A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
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title_short | A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
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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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