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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4305 - 4314

DOI: https://doi.org/10.6023/cjoc202005080

Fully Substituted Pyrazoles Assisted Palladium-Catalyzed Late-Stage Arylation of C(sp2)—H Bond

  • Fu Xiaopan ,
  • Wang Yangyang ,
  • Yang Jinyue ,
  • Wu Gaorong ,
  • Xia Chengcai ,
  • Ji Yafei
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  • a Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science & Technology, Shanghai 200237;
    b Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian, Shandong 271016

Received date: 2020-05-28

  Revised date: 2020-06-28

  Online published: 2020-07-23

Supported by

Project supported by the National Natural Science Foundation of China (No. 21676088).

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Abstract

A successful protocol has been developed for palladium-catalyzed late-stage arylation of fully substituted pyrazoles. Through screening of optimazation of reaction parameters, the most efficient reaction conditions for mono-ortho-position arylation were obtained. This reaction features a broad substrate scope, good functional group tolerance as well as good to excellent yield. Moreover, the intermolecular competition experiments and gram scale reaction were also performed. The kinetic isotopic effect (KIE) result reveled C-H bond cleavage was involved in the rate-limiting step and a plausible mechanism was proposed based on the dual-core dimeric palladacycle.

Key words： mono-arylation; late-stage functionalization; fully substituted pyrazole; C(sp2)-H bond

Cite this article

Fu Xiaopan , Wang Yangyang , Yang Jinyue , Wu Gaorong , Xia Chengcai , Ji Yafei . Fully Substituted Pyrazoles Assisted Palladium-Catalyzed Late-Stage Arylation of C(sp2)—H Bond[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4305 -4314 . DOI: 10.6023/cjoc202005080

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