Paired electrocatalysis unlocks cross-dehydrogenative coupling of C(sp3)-H bonds using a pentacoordinated cobalt-salen catalyst

Ke Liu, Mengna Lei, Xin Li, Xuemei Zhang, Ying Zhang, Weigang Fan, Man-Bo Li () and Sheng Zhang ()
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Ke Liu: Anhui University
Mengna Lei: Anhui University
Xin Li: Anhui University
Xuemei Zhang: Anhui University
Ying Zhang: Anhui University
Weigang Fan: Anhui University
Man-Bo Li: Anhui University
Sheng Zhang: Anhui University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Cross-dehydrogenative coupling of C(sp3)-H bonds is an ideal approach for C(sp3)-C(sp3) bond construction. However, conventional approaches mainly rely on a single activation mode by either stoichiometric oxidants or electrochemical oxidation, which would lead to inferior selectivity in the reaction between similar C(sp3)-H bonds. Herein we describe our development of a paired electrocatalysis strategy to access an unconventional selectivity in the cross-dehydrogenative coupling of alcoholic α C(sp3)-H with allylic (or benzylic) C-H bonds, which combines hydrogen evolution reaction catalysis with hydride transfer catalysis. To maximize the synergistic effect of the catalyst combinations, a HER catalyst pentacoordinated Co-salen is disclosed. The catalyst displays a large redox-potential gap (1.98 V) and suitable redox potential. With the optimized catalyst combination, an electrochemical cross-dehydrogenative coupling protocol features unconventional chemoselectivity (C-C vs. C-O coupling), excellent functional group tolerance (84 examples), valuable byproduct (hydrogen), and high regio- and site-selectivity. A plausible reaction mechanism is also proposed to rationalize the experimental observations.

Date: 2024
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DOI: 10.1038/s41467-024-47220-9

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