有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2462-2470.DOI: 10.6023/cjoc202204014 上一篇    下一篇

研究论文

可见光诱导α-重氮酯的脱氮氧合反应构建α-氧代酰亚胺酯

刘瑞生a, 付双敏a, 楚秀民a, 张灵莉a, 丁柔a, 赵先恩a, 岳会兰b,*(), 魏伟a,b,*()   

  1. a 曲阜师范大学化学与化工学院 山东曲阜 273165
    b 中国科学院藏药研究重点实验室 中国科学院西北高原生物研究所 青海西宁 810008
  • 收稿日期:2022-04-06 修回日期:2022-05-02 发布日期:2022-05-17
  • 通讯作者: 岳会兰, 魏伟
  • 作者简介:
    共同第一作者
  • 基金资助:
    国家级大学生创新创业训练项目(S202110446110); 山东省高校青创科技计划(2019KJC021); 山东省自然科学基金(ZR2021MB065); 国家自然科学基金(22176109); 国家自然科学基金(31900298); 青海省创新平台建设专项(2022-ZJ-Y03)

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

Ruisheng Liua, Shuangmin Fua, Xiumin Chua, Lingli Zhanga, Rou Dinga, Xian'en Zhaoa, Huilan Yueb(), Wei Weia,b()   

  1. 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
  • Received:2022-04-06 Revised:2022-05-02 Published:2022-05-17
  • Contact: Huilan Yue, Wei Wei
  • About author:
    These authors contributed equally to this work.
  • 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)

报道了一种可见光诱导下α-重氮酯与N-羟基邻苯二甲酰亚胺(NHI)的脱氮氧合反应构建α-氧代酰亚胺酯化合物的方法. 该反应采用3W蓝色LEDs灯为可见光源, 无需任何光催化剂, 室温下在1,4-二氧六环溶剂中可以有效合成一系列α-氧代酰亚胺酯化合物. 有趣的是, 当四氢呋喃作为溶剂时, 四氢呋喃参与的三组分开环产物可以获得中等至良好的收率. 该反应放大到克级规模仍保持良好的反应效率, 表明该方法具有合成α-氧代酰亚胺酯的实际应用潜力.

关键词: 可见光, α-重氮酯, N-羟基邻苯二甲酰亚胺, α-氧代酰亚胺酯

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