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Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds

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Abstract

Convergent paired electrosynthesis is an energy-efficient approach in organic synthesis; however, it is limited by the difficulty to match the innate redox properties of reaction partners. Here we use nickel catalysis to cross-couple the two intermediates generated at the two opposite electrodes of an electrochemical cell, achieving direct arylation of benzylic C–H bonds. This method yields a diverse set of diarylmethanes, which are important structural motifs in medicinal and materials chemistry. Preliminary mechanistic study suggests oxidation of a benzylic C–H bond, Ni-catalyzed C–C coupling, and reduction of a Ni intermediate as key elements of the catalytic cycle.

Graphical abstract: Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds

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Article information


Submitted
10 Mar 2020
Accepted
24 Apr 2020
First published
27 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds

L. Zhang and X. Hu, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC01445A

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