无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺

doi:10.6023/cjoc202006030

有机化学 ›› 2020, Vol. 40 ›› Issue (12): 4284-4289.DOI: 10.6023/cjoc202006030 上一篇下一篇

研究论文

无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺

谢建伟^a,b, 沈丽^b, 张洁^b, 龚绍峰^a

a 湖南科技学院化学与生物工程学院湖南永州 425199;
b 石河子大学化学化工学院新疆石河子 832003

收稿日期:2020-06-17 修回日期:2020-07-13 发布日期:2020-08-01
通讯作者: 谢建伟, 龚绍峰 E-mail:cesxjw@foxmail.com;simon.gong@huse.edu.cn
基金资助:
国家自然科学基金（No.21868032）和新疆兵团材料化工工程技术研究中心开放基金（No.2019BTRC001）资助项目.

Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides

Xie Jianwei^a,b, Shen Li^b, Zhang Jie^b, Gong Shaofeng^a

a College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199;
b School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2020-06-17 Revised:2020-07-13 Published:2020-08-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21868032) and the Opening Foundation of Engineering Research Center of Materials-Oriented Chemical Engineering of Xinjiang Bingtuan (No. 2019BTRC001).

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摘要/Abstract

报道了一种无过渡金属条件下，α-芳香酮酸和叠氮磷酸二苯酯（DPPA）发生脱羧偶联制备芳香伯酰胺的方法.该方法条件温和，无需惰性气体保护，各种取代芳香α-酮酸均可顺利反应得到优良的分离产率，体现了较好的官能团适应性.克量级实验在该反应条件下也可顺利实现，以高产率生成目标产物，同时对反应机理也进行了探究.

关键词: 脱羧酰胺化反应, 伯酰胺, 叠氮磷酸二苯酯, α-芳香酮酸, 无过渡金属

In this paper, a novel transition-metal-free decarboxylative amidation of aryl α-keto acids with diphenylphosphoryl azide (DPPA) under mild conditions has been developed. The reaction proceeded smoothly to afford the corresponding primary aryl amide products in good to excellent yields under air and showed excellent functional group tolerance. Gram-scale reaction was also performed to produce the desired product in high yield. In addition, the mechanism of the present reaction was investigated.

Key words: decarboxylative amidation, primary amides, diphenylphosphoryl azide, α-keto acids, transition-metal-free

引用此文

谢建伟, 沈丽, 张洁, 龚绍峰. 无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺[J]. 有机化学, 2020, 40(12): 4284-4289.

Xie Jianwei, Shen Li, Zhang Jie, Gong Shaofeng. Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4284-4289.

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无过渡金属条件下α-芳香酮酸与叠氮磷酸二苯酯脱羧酰胺化制备芳香伯酰胺

Transition-Metal-Free Decarboxylative Amidation of Aryl α-Keto Acids with Diphenylphosphoryl Azide: New Avenue for the Preparation of Primary Aryl Amides

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