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A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation
An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method d...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9116295/ https://www.ncbi.nlm.nih.gov/pubmed/35694363 http://dx.doi.org/10.1039/d2sc01363k |
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author | Sharique, Mohammed Majhi, Jadab Dhungana, Roshan K. Kammer, Lisa Marie Krumb, Matthias Lipp, Alexander Romero, Eugénie Molander, Gary A. |
author_facet | Sharique, Mohammed Majhi, Jadab Dhungana, Roshan K. Kammer, Lisa Marie Krumb, Matthias Lipp, Alexander Romero, Eugénie Molander, Gary A. |
author_sort | Sharique, Mohammed |
collection | PubMed |
description | An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate. |
format | Online Article Text |
id | pubmed-9116295 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-91162952022-06-10 A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation Sharique, Mohammed Majhi, Jadab Dhungana, Roshan K. Kammer, Lisa Marie Krumb, Matthias Lipp, Alexander Romero, Eugénie Molander, Gary A. Chem Sci Chemistry An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate. The Royal Society of Chemistry 2022-04-26 /pmc/articles/PMC9116295/ /pubmed/35694363 http://dx.doi.org/10.1039/d2sc01363k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Sharique, Mohammed Majhi, Jadab Dhungana, Roshan K. Kammer, Lisa Marie Krumb, Matthias Lipp, Alexander Romero, Eugénie Molander, Gary A. A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title | A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title_full | A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title_fullStr | A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title_full_unstemmed | A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title_short | A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation |
title_sort | practical and sustainable two-component minisci alkylation via photo-induced eda-complex activation |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9116295/ https://www.ncbi.nlm.nih.gov/pubmed/35694363 http://dx.doi.org/10.1039/d2sc01363k |
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