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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4284 - 4289

DOI: https://doi.org/10.6023/cjoc202006030

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

  • Xie Jianwei ,
  • Shen Li ,
  • Zhang Jie ,
  • Gong Shaofeng
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  • 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 date: 2020-06-17

  Revised date: 2020-07-13

  Online 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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Abstract

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

Cite this article

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

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