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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 8: 2462 - 2470

DOI: https://doi.org/10.6023/cjoc202204014

ARTICLES

Visible-Light-Induced Denitrification Oxygenation Reaction of α-Diazoesters to Construct α-Oxyimido Esters

  • Ruisheng Liu ,
  • Shuangmin Fu ,
  • Xiumin Chu ,
  • Lingli Zhang ,
  • Rou Ding ,
  • Xian'en Zhao ,
  • Huilan Yue ,
  • Wei Wei
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  • a School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
    b CAS Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, Qinghai 810008
† These authors contributed equally to this work.
* E-mail: ;

Received date: 2022-04-06

  Revised date: 2022-05-02

  Online published: 2022-05-18

Supported by

National Training Programs of Innovation and Entrepreneurship for Undergraduates(S202110446110); Youth Innovation and Technology Project of High School in Shandong Province(2019KJC021); Natural Science Foundation of Shandong Province(ZR2021MB065); National Natural Science Foundation of China(22176109); National Natural Science Foundation of China(31900298); Innovation Platform Construction Project of Qinghai Province(2022-ZJ-Y03)

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Abstract

Visible-light-induced denitrification oxygenation reaction of α-diazoesters with N-hydroxyimides to access α-oxyimido esters has been developed. This reaction provides an efficient approach to synthesize a series of N-hydroxyimides at room temperature in 1,4-dioxane under irradiation of 3W blue LED lamps without any photocatalyst. Interestingly, when tetrahydrofuran (THF) was used as the solvent, structurally diverse α-oxyimido esters could be rapidly and efficiently obtained through a three-component coupling reaction of α-diazoesters, THF, and N-hydroxyimides. The reaction could conduct on a gram scale without a significant loss of reaction efficiency, indicating that this method could serve as a practical protocol to synthesize α-oxyimido esters.

Key words： visible-light; α-diazoester; N-hydroxyphthalimide; α-oxoimide ester

Cite this article

Ruisheng Liu , Shuangmin Fu , Xiumin Chu , Lingli Zhang , Rou Ding , Xian'en Zhao , Huilan Yue , Wei Wei . Visible-Light-Induced Denitrification Oxygenation Reaction of α-Diazoesters to Construct α-Oxyimido Esters[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2462 -2470 . DOI: 10.6023/cjoc202204014

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