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Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis
[Image: see text] A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted pai...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8395614/ https://www.ncbi.nlm.nih.gov/pubmed/34467349 http://dx.doi.org/10.1021/jacsau.1c00148 |
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author | Zhu, Chen Kale, Ajit Prabhakar Yue, Huifeng Rueping, Magnus |
author_facet | Zhu, Chen Kale, Ajit Prabhakar Yue, Huifeng Rueping, Magnus |
author_sort | Zhu, Chen |
collection | PubMed |
description | [Image: see text] A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when benzophenone imine is applied in the arylation, the product selectivity toward the formation of amine and imine product can be addressed by a base switch. In addition, the alternating current mode can be successfully applied. DFT calculations support a facilitated reductive elimination pathway. |
format | Online Article Text |
id | pubmed-8395614 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-83956142021-08-30 Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis Zhu, Chen Kale, Ajit Prabhakar Yue, Huifeng Rueping, Magnus JACS Au [Image: see text] A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when benzophenone imine is applied in the arylation, the product selectivity toward the formation of amine and imine product can be addressed by a base switch. In addition, the alternating current mode can be successfully applied. DFT calculations support a facilitated reductive elimination pathway. American Chemical Society 2021-06-15 /pmc/articles/PMC8395614/ /pubmed/34467349 http://dx.doi.org/10.1021/jacsau.1c00148 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Zhu, Chen Kale, Ajit Prabhakar Yue, Huifeng Rueping, Magnus Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis |
title | Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines,
Carbamates, and Imines via Nickelaelectrocatalysis |
title_full | Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines,
Carbamates, and Imines via Nickelaelectrocatalysis |
title_fullStr | Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines,
Carbamates, and Imines via Nickelaelectrocatalysis |
title_full_unstemmed | Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines,
Carbamates, and Imines via Nickelaelectrocatalysis |
title_short | Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines,
Carbamates, and Imines via Nickelaelectrocatalysis |
title_sort | redox-neutral cross-coupling amination with weak n-nucleophiles: arylation of anilines, sulfonamides, sulfoximines,
carbamates, and imines via nickelaelectrocatalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8395614/ https://www.ncbi.nlm.nih.gov/pubmed/34467349 http://dx.doi.org/10.1021/jacsau.1c00148 |
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