Citation: 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. doi: 10.6023/cjoc202006030 shu

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

Corresponding author: Xie Jianwei, cesxjw@foxmail.com Gong Shaofeng, simon.gong@huse.edu.cn
Received Date: 17 June 2020
Revised Date: 13 July 2020
Available Online: 30 July 2020
Fund Project: the National Natural Science Foundation of China 21868032the Opening Foundation of Engineering Research Center of Materials-Oriented Chemical Engineering of Xinjiang Bingtuan 2019BTRC001Project 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)

Figures(4)

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.
- decarboxylative amidation,
- primary amides,
- diphenylphosphoryl azide,
- α-keto acids,
- transition-metal-free
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