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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 3: 651 - 662

DOI: https://doi.org/10.6023/cjoc201911016

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

  • Shuai Bin ,
  • Li Zhao-Ming ,
  • Qiu Hui ,
  • Fang Ping ,
  • Mei Tian-Sheng
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  • 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 date: 2019-11-08

  Revised date: 2019-12-11

  Online 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).

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Abstract

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

Cite this article

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

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