Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2

Guo-Quan Sun, Wei Zhang, Li-Li Liao, Li Li, Zi-Hao Nie, Jin-Gui Wu, Zhen Zhang and Da-Gang Yu ()
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Guo-Quan Sun: Sichuan University
Wei Zhang: Sichuan University
Li-Li Liao: Sichuan University
Li Li: Sichuan University
Zi-Hao Nie: Sichuan University
Jin-Gui Wu: Sichuan University
Zhen Zhang: Chengdu University
Da-Gang Yu: Sichuan University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Electrochemical catalytic reductive cross couplings are powerful and sustainable methods to construct C−C bonds by using electron as the clean reductant. However, activated substrates are used in most cases. Herein, we report a general and practical electro-reductive Ni-catalytic system, realizing the electrocatalytic carboxylation of unactivated aryl chlorides and alkyl bromides with CO2. A variety of unactivated aryl bromides, iodides and sulfonates can also undergo such a reaction smoothly. Notably, we also realize the catalytic electrochemical carboxylation of aryl (pseudo)halides with CO2 avoiding the use of sacrificial electrodes. Moreover, this sustainable and economic strategy with electron as the clean reductant features mild conditions, inexpensive catalyst, safe and cheap electrodes, good functional group tolerance and broad substrate scope. Mechanistic investigations indicate that the reaction might proceed via oxidative addition of aryl halides to Ni(0) complex, the reduction of aryl-Ni(II) adduct to the Ni(I) species and following carboxylation with CO2.

Date: 2021
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DOI: 10.1038/s41467-021-27437-8

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