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General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides

Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors. Primary, secondary and tertiary alkyl radicals have been shown to be eff...

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Autores principales: del Río-Rodríguez, Roberto, Fragoso-Jarillo, Lorena, Garrido-Castro, Alberto F., Maestro, M. Carmen, Fernández-Salas, Jose A., Alemán, José
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/PMC9172443/
https://www.ncbi.nlm.nih.gov/pubmed/35756520
http://dx.doi.org/10.1039/d2sc01799g
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author del Río-Rodríguez, Roberto
Fragoso-Jarillo, Lorena
Garrido-Castro, Alberto F.
Maestro, M. Carmen
Fernández-Salas, Jose A.
Alemán, José
author_facet del Río-Rodríguez, Roberto
Fragoso-Jarillo, Lorena
Garrido-Castro, Alberto F.
Maestro, M. Carmen
Fernández-Salas, Jose A.
Alemán, José
author_sort del Río-Rodríguez, Roberto
collection PubMed
description Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors. Primary, secondary and tertiary alkyl radicals have been shown to be efficiently generated and coupled with a large variety of N-heteroarenes. The method presents a very high functional group tolerance, including various heterocyclic-based natural products, which highlights the robustness of the methodology. This applicability has been further proved in the synthesis of various interesting biologically valuable building blocks. In addition, we have proposed a mechanism based on different proofs and pieces of electrochemical evidence.
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spelling pubmed-91724432022-06-23 General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides del Río-Rodríguez, Roberto Fragoso-Jarillo, Lorena Garrido-Castro, Alberto F. Maestro, M. Carmen Fernández-Salas, Jose A. Alemán, José Chem Sci Chemistry Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of N-heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors. Primary, secondary and tertiary alkyl radicals have been shown to be efficiently generated and coupled with a large variety of N-heteroarenes. The method presents a very high functional group tolerance, including various heterocyclic-based natural products, which highlights the robustness of the methodology. This applicability has been further proved in the synthesis of various interesting biologically valuable building blocks. In addition, we have proposed a mechanism based on different proofs and pieces of electrochemical evidence. The Royal Society of Chemistry 2022-05-06 /pmc/articles/PMC9172443/ /pubmed/35756520 http://dx.doi.org/10.1039/d2sc01799g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
del Río-Rodríguez, Roberto
Fragoso-Jarillo, Lorena
Garrido-Castro, Alberto F.
Maestro, M. Carmen
Fernández-Salas, Jose A.
Alemán, José
General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title_full General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title_fullStr General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title_full_unstemmed General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title_short General electrochemical Minisci alkylation of N-heteroarenes with alkyl halides
title_sort general electrochemical minisci alkylation of n-heteroarenes with alkyl halides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9172443/
https://www.ncbi.nlm.nih.gov/pubmed/35756520
http://dx.doi.org/10.1039/d2sc01799g
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