Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Bortnikov, Evgeniy O., Semenov, Sergey N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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
_version_ 1783632168581332992
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