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Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling
[Image: see text] The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to alternating current (AC) thro...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783731/ https://www.ncbi.nlm.nih.gov/pubmed/33186048 http://dx.doi.org/10.1021/acs.joc.0c02350 |
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author | Bortnikov, Evgeniy O. Semenov, Sergey N. |
author_facet | Bortnikov, Evgeniy O. Semenov, Sergey N. |
author_sort | Bortnikov, Evgeniy O. |
collection | PubMed |
description | [Image: see text] The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to alternating current (AC) through electron transfer steps that occur periodically at the same electrode. AC-assisted Ni-catalyzed amination, etherification, and esterification of aromatic bromides showed higher yields and selectivity compared to that observed in the control experiments with direct current. Our mechanistic studies suggested the importance of both reduction and oxidation processes in the maintenance of the AC-assisted catalytic reactions. As described in presented examples, the AC assistance should be well-suited for catalytic cycles involving reductive elimination or oxidative addition as a limiting step. |
format | Online Article Text |
id | pubmed-7783731 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-77837312021-01-06 Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling Bortnikov, Evgeniy O. Semenov, Sergey N. J Org Chem [Image: see text] The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to alternating current (AC) through electron transfer steps that occur periodically at the same electrode. AC-assisted Ni-catalyzed amination, etherification, and esterification of aromatic bromides showed higher yields and selectivity compared to that observed in the control experiments with direct current. Our mechanistic studies suggested the importance of both reduction and oxidation processes in the maintenance of the AC-assisted catalytic reactions. As described in presented examples, the AC assistance should be well-suited for catalytic cycles involving reductive elimination or oxidative addition as a limiting step. American Chemical Society 2020-11-13 2021-01-01 /pmc/articles/PMC7783731/ /pubmed/33186048 http://dx.doi.org/10.1021/acs.joc.0c02350 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Bortnikov, Evgeniy O. Semenov, Sergey N. Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title | Coupling of Alternating
Current to Transition-Metal
Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title_full | Coupling of Alternating
Current to Transition-Metal
Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title_fullStr | Coupling of Alternating
Current to Transition-Metal
Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title_full_unstemmed | Coupling of Alternating
Current to Transition-Metal
Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title_short | Coupling of Alternating
Current to Transition-Metal
Catalysis: Examples of Nickel-Catalyzed Cross-Coupling |
title_sort | coupling of alternating
current to transition-metal
catalysis: examples of nickel-catalyzed cross-coupling |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783731/ https://www.ncbi.nlm.nih.gov/pubmed/33186048 http://dx.doi.org/10.1021/acs.joc.0c02350 |
work_keys_str_mv | AT bortnikovevgeniyo couplingofalternatingcurrenttotransitionmetalcatalysisexamplesofnickelcatalyzedcrosscoupling AT semenovsergeyn couplingofalternatingcurrenttotransitionmetalcatalysisexamplesofnickelcatalyzedcrosscoupling |