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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...

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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
Descripción
Sumario:[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.