Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides

Dong Liu, Zhao-Ran Liu, Zhen-Hua Wang, Cong Ma, Simon Herbert, Hartmut Schirok and Tian-Sheng Mei ()
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Dong Liu: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS
Zhao-Ran Liu: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS
Zhen-Hua Wang: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS
Cong Ma: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS
Simon Herbert: Bayer AG
Hartmut Schirok: Bayer AG
Tian-Sheng Mei: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Electrochemical asymmetric catalysis has emerged as a sustainable and promising approach to the production of chiral compounds and the utilization of both the anode and cathode as working electrodes would provide a unique approach for organic synthesis. However, precise matching of the rate and electric potential of anodic oxidation and cathodic reduction make such idealized electrolysis difficult to achieve. Herein, asymmetric cross-coupling between α-chloroesters and aryl bromides is probed as a model reaction, wherein alkyl radicals are generated from the α-chloroesters through a sequential oxidative electron transfer process at the anode, while the nickel catalyst is reduced to a lower oxidation state at the cathode. Radical clock studies, cyclic voltammetry analysis, and electron paramagnetic resonance experiments support the synergistic involvement of anodic and cathodic redox events. This electrolytic method provides an alternative avenue for asymmetric catalysis that could find significant utility in organic synthesis.

Date: 2022
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DOI: 10.1038/s41467-022-35073-z

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