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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...
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/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. |
format | Online Article Text |
id | pubmed-9172443 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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