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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...

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Autores principales: Sharique, Mohammed, Majhi, Jadab, Dhungana, Roshan K., Kammer, Lisa Marie, Krumb, Matthias, Lipp, Alexander, Romero, Eugénie, Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
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.
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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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