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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...

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Detalles Bibliográficos
Autores principales: Samanta, Ramesh C., Struwe, Julia, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
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.
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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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