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
收稿日期: 2022-04-06
修回日期: 2022-05-02
网络出版日期: 2022-05-18
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
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)
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
刘瑞生 , 付双敏 , 楚秀民 , 张灵莉 , 丁柔 , 赵先恩 , 岳会兰 , 魏伟 . 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[J]. 有机化学, 2022 , 42(8) : 2462 -2470 . DOI: 10.6023/cjoc202204014
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
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