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Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature
Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel‐catalyzed C−H alkylations of unactivated 8‐aminoquinoline amides have been reali...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496282/ https://www.ncbi.nlm.nih.gov/pubmed/32324948 http://dx.doi.org/10.1002/anie.202004958 |
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author | Samanta, Ramesh C. Struwe, Julia Ackermann, Lutz |
author_facet | Samanta, Ramesh C. Struwe, Julia Ackermann, Lutz |
author_sort | Samanta, Ramesh C. |
collection | PubMed |
description | Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel‐catalyzed C−H alkylations of unactivated 8‐aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user‐friendly electrochemical setup. This electrocatalyzed C−H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed. |
format | Online Article Text |
id | pubmed-7496282 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74962822020-09-25 Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature Samanta, Ramesh C. Struwe, Julia Ackermann, Lutz Angew Chem Int Ed Engl Communications Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel‐catalyzed C−H alkylations of unactivated 8‐aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user‐friendly electrochemical setup. This electrocatalyzed C−H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed. John Wiley and Sons Inc. 2020-06-08 2020-08-10 /pmc/articles/PMC7496282/ /pubmed/32324948 http://dx.doi.org/10.1002/anie.202004958 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Samanta, Ramesh C. Struwe, Julia Ackermann, Lutz Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title | Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title_full | Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title_fullStr | Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title_full_unstemmed | Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title_short | Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature |
title_sort | nickela‐electrocatalyzed mild c−h alkylations at room temperature |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496282/ https://www.ncbi.nlm.nih.gov/pubmed/32324948 http://dx.doi.org/10.1002/anie.202004958 |
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