C—N Coupling Reactions between Benzophenone Hydrazone and Aryl Chlorides and Boronic Acids

doi:10.6023/cjoc201912038

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1673-1679.DOI: 10.6023/cjoc201912038 Previous Articles Next Articles

二苯甲酮腙与芳基氯化物及芳基硼酸的碳氮键偶联反应

姚丹丹, 张金利, 徐亮

石河子大学化学化工学院新疆兵团化工绿色过程重点实验室新疆石河子 832003

收稿日期:2019-12-26 修回日期:2020-02-21 发布日期:2020-03-06
通讯作者: 张金利, 徐亮 E-mail:zhangjinli@tju.edu.cn;xuliang4423@shzu.edu.cn
基金资助:
国家自然科学基金（Nos.21603150，21963010）资助项目.

C—N Coupling Reactions between Benzophenone Hydrazone and Aryl Chlorides and Boronic Acids

Yao Dandan, Zhang Jinli, Xu Liang

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2019-12-26 Revised:2020-02-21 Published:2020-03-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21603150, 21963010).

1. 201673S.pdf(2395KB)

Abstract

Palladium catalyzed Buchwald-Hartwig reactions between aryl halides and N-nucleophiles, and the copper catalyzed Chan-Evans-Lam reactions between aryl boronic acids and N-nucleophiles are all effective methods for constructing C-N bonds. Herein, under palladium acetate/tert-butanol system or copper acetate/dichloromethane system, benzophenone hydrazone can react with aryl chlorides and aryl boronic acids to afford corresponding aryl hydrazones, respectively. The obtained products are easily hydrolyzed to form aryl hydrazines, thus providing an indirect pathway to access aryl hydrazines from relatively less toxic reagents.

Key words: Buchwald-Hartwig reaction, Chan-Evans-Lam reaction, aryl boronic acid, benzophenone hydrazone

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Yao Dandan, Zhang Jinli, Xu Liang. C—N Coupling Reactions between Benzophenone Hydrazone and Aryl Chlorides and Boronic Acids[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1673-1679.

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二苯甲酮腙与芳基氯化物及芳基硼酸的碳氮键偶联反应

C—N Coupling Reactions between Benzophenone Hydrazone and Aryl Chlorides and Boronic Acids

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