Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 651-662.DOI: 10.6023/cjoc201911016 Previous Articles     Next Articles

Special Issue: 镍催化有机反应合辑


帅斌, 李兆明, 裘晖, 方萍, 梅天胜   

  1. 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 分子合成科学卓越中心中国科学院大学 上海 200032
  • 收稿日期:2019-11-08 修回日期:2019-12-11 发布日期:2019-12-19
  • 通讯作者: 方萍, 梅天胜;
  • 基金资助:

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

Shuai Bin, Li Zhao-Ming, Qiu Hui, Fang Ping, Mei Tian-Sheng   

  1. 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
  • Received:2019-11-08 Revised:2019-12-11 Published:2019-12-19
  • Supported by:
    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).

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.

Key words: Negishi coupling, nickel, cyclobutanone oxime esters, aryl zinc reagents