Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3154-3161.DOI: 10.6023/cjoc201904062 Previous Articles     Next Articles

Special Issue: 碳氢活化合辑2018-2019

钯催化噻唑定位基导向的单选择性C(sp2)-H键碘化反应

  

  • 收稿日期:2019-04-25 出版日期:2019-11-25 发布日期:2019-06-19

Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp2)-H Bond Iodination Reaction

Xing Lihao, Shao Lingyan*(), Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei*()   

  1. School of Pharmacy, East China University of Science & Technology, Shanghai 200237
  • Received:2019-04-25 Online:2019-11-25 Published:2019-06-19
  • Contact: Shao Lingyan,Ji Yafei E-mail:shaoly520@163.com;jyf@ecust.edu.cn
  • Supported by:
    the National Science Foundation of China(21676088);the National Science Foundation of China(21476074)

A palladium-catalyzed ortho-C(sp2)-H bond iodination of 4-arylthiazoles has been developed. Through screening of directing groups and optimazation of reaction parameters, the most efficient reaction conditions for mono-ortho-position iodination were obtained, which were applied to synthesize a series of 4-(2-iodoaryl)thiazoles with broad scope of 4-aryl-thiazole substrates. Furthermore, the iodine group can be easily transformed into other organic functional groups, which improved the application value of this methodology. At last, plausible mechanism was proposed based on an intermolecular deuterium labeling kinetic experiment and radical inhibition experiments.

Key words: palladium-catalyzed, 4-arylthiazoles, mono-selectivity, C(sp2)-H bond, iodination