Citation: Shuai Bin, Li Zhao-Ming, Qiu Hui, Fang Ping, Mei Tian-Sheng. Nickel-Catalyzed Negishi Coupling of Cyclobutanone Oxime Esters with Aryl Zinc Reagents[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 651-662. doi: 10.6023/cjoc201911016 shu

Nickel-Catalyzed Negishi Coupling of Cyclobutanone Oxime Esters with Aryl Zinc Reagents

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Fang Ping, pfang@sioc.ac.cn Mei Tian-Sheng, mei7900@sioc.ac.cn
Received Date: 8 November 2019
Revised Date: 11 December 2019
Available Online: 19 December 2019
Fund Project: Project supported by the Strategic Priority Research Program (No. XDB20000000), the National Natural Science Foundation of China (Nos. 21572245, 21772222, 21772220), and the Shanghai Committee of Science and Technology (Nos. 17JC1401200, 18JC1415600)the Shanghai Committee of Science and Technology 18JC1415600the Shanghai Committee of Science and Technology 17JC1401200the Strategic Priority Research Program XDB20000000the National Natural Science Foundation of China 21772222the National Natural Science Foundation of China 21772220the National Natural Science Foundation of China 21572245

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A nickel-catalyzed Negishi coupling of cyclobutanone oxime esters with aryl zinc reagents has been developed, in which nickel serves both as an initiator for imine radicals and a catalyst for the coupling of aryl zinc reagents with oxime esters. The protocol can avoid the use of poisonous cyanide and has broad substrate scope as well as good functional group compatibility. Therefore, this method provides an attractive strategy for the synthesis of valuable nitriles. Preliminary mechanistic studies indicate that a radical pathway is involved in the product formation.
- Negishi coupling,
- nickel,
- cyclobutanone oxime esters,
- aryl zinc reagents
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