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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 11: 3154 - 3161

DOI: https://doi.org/10.6023/cjoc201904062

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

  • Lihao Xing ,
  • Lingyan Shao ,
  • Xiaopan Fu ,
  • Kezuan Deng ,
  • Jinyue Yang ,
  • Yafei Ji
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  • School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Received date: 2019-04-25

  Online published: 2019-06-19

Supported by

the National Science Foundation of China(21676088);the National Science Foundation of China(21476074)

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Abstract

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

Cite this article

Lihao Xing , Lingyan Shao , Xiaopan Fu , Kezuan Deng , Jinyue Yang , Yafei Ji . Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp2)-H Bond Iodination Reaction[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 3154 -3161 . DOI: 10.6023/cjoc201904062

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