Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling

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Abstract

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.
Original languageEnglish
Pages (from-to)782-793
Number of pages12
JournalJournal of Organic Chemistry
Volume86
Issue number1
Early online date13 Nov 2020
DOIs
Publication statusPublished - 1 Jan 2021

Funding

We thank E. Narevicius for the help with setting up equipment for AC experiments. We thank R. Neumann and M. Somekh for helpful discussions.

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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