Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2171-2177.DOI: 10.6023/cjoc202208006 Previous Articles     Next Articles


秦娇, 陈杰, 苏艳*()   

  1. 宁夏大学化学化工学院 省部共建煤炭高效利用与绿色化工国家重点实验室 银川 750021
  • 收稿日期:2022-08-05 修回日期:2022-10-31 发布日期:2022-12-28
  • 作者简介:
  • 基金资助:

Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone

Jiao Qin, Jie Chen, Yan Su*()   

  1. State Key Laboratory of High-Efficiency Coal Utilization and Green Chemical Engineering, College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021
  • Received:2022-08-05 Revised:2022-10-31 Published:2022-12-28
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  • About author:
    The authors contributed equally to this work
  • Supported by:
    Ningxia Natural Science Foundation(2021AAC03100)

In this paper, the synthesis of 2,2,6,6-tetramethylpiperidin-1-yl-2-(2-cyanophenyl)acetate from bromoindanone with sodium azide and 2,2,6,6-tetramethylpiperidine nitrogen oxide was reported. The carbon-carbon bond cleavage of bromoindenone was realized with transition metal-free catalysis and a series of aryl 2-cyano-phenylacetate compounds were obtained. This method was an expansion of cyanophenylacetate’ synthesis, and the reaction mechanism was verified by computational chemistry. The experiment was carried out under mild conditions with transition metal-free catalysis and with broad substrate scope.

Key words: indanone, 2-cyanophenylacetate, radical cleavage reaction, transition metal-free