Citation: Xing Lihao, Shao Lingyan, Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei. 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 shu

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

School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Corresponding author: Shao Lingyan, shaoly520@163.com Ji Yafei, jyf@ecust.edu.cn
Received Date: 25 April 2019
Revised Date: 2 June 2019
Available Online: 19 November 2019
Fund Project: the National Science Foundation of China 21476074Project supported by the National Science Foundation of China (Nos. 21676088, 21476074)the National Science Foundation of China 21676088

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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.
- palladium-catalyzed,
- 4-arylthiazoles,
- mono-selectivity,
- C(sp²)-H bond,
- iodination
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沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

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