Citation: Yuqing Zhong, Mengmeng Jiang, Deyong Yang, Nan Feng, Ying Sun, Huimin Wang, Feng Zhou. Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO₂ to 2,3-allenoic acids[J]. Chinese Chemical Letters, ;2025, 36(12): 111169. doi: 10.1016/j.cclet.2025.111169 shu

Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO₂ to 2,3-allenoic acids

State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China

fzhou@chem.ecnu.edu.cn

Received Date: 22 January 2025
Revised Date: 18 March 2025
Accepted Date: 1 April 2025
Available Online: 2 April 2025

Figures(3)

Here, we report a novel nickel-catalyzed electrochemical carboxylation of propargylic esters with CO₂, characterized by the regioselective synthesis of 2,3-allenoic acids rather than propargylic carboxylic acids. Both acyclic propargylic esters and cyclic propargylic carbonates serve as effective substrates, facilitating the synthesis of mono-, di-, tri-, and tetra-substituted 2,3-allenoic acids with broad substrate scope under mild conditions. Mechanistic investigations indicate that the in situ generated Ni(Ⅰ) complex might serve as the active species to react with propargylic esters, forming the allenyl-Ni(Ⅰ) complex under electro-reductive conditions. A possible γ-selective nucleophilic attack of allenyl-Ni(Ⅰ) complex on CO₂ is likely involved in the formation of the desired 2,3-allenoic acids.
- CO₂,
- Nickel-catalysis,
- Electro-carboxylation,
- Propargylic esters,
- 2,3-Allenoic acids
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO2 to 2,3-allenoic acids

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通讯作者: 陈斌, bchen63@163.com

Nickel-catalyzed electrochemical carboxylation of propargylic esters with CO₂ to 2,3-allenoic acids