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

doi:10.6023/cjoc202204014

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2462-2470.DOI: 10.6023/cjoc202204014 Previous Articles Next Articles

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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^,^*()

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 Liu^a, Shuangmin Fu^a, Xiumin Chu^a, Lingli Zhang^a, Rou Ding^a, Xian'en Zhao^a, Huilan Yue^b(), Wei Wei^a^,^b()

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)

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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.

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References 21

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Entry	Photocatalyst	Solvent	Yield^b/%
Entry	Photocatalyst	Solvent	3a		4a
1	Eosin Y	CH₂Cl₂	72	0
2	Rose Bengal	CH₂Cl₂	39	0
3	4CzIPN	CH₂Cl₂	70	0
4	—	CH₂Cl₂	74	0
5	—	DMF	0	0
6	—	DMSO	0	0
7	—	CH₃CN	48	0
8	—	DCE	33	0
9	—	CHCl₃	26	0
10	—	Acetone	43	0
11	—	AcOEt	38	0
12	—	1,4-Dioxane	76	0
13	—	THF	0	98
14	—	1,4-Dioxane	15^c	0
15	—	1,4-Dioxane	10^d	0
16	—	1,4-Dioxane	18^e	0
17	—	1,4-Dioxane	0^f	0
18	—	THF	0	0^f

Entry	Photocatalyst	Solvent	Yield^b/%
Entry	Photocatalyst	Solvent	3a		4a
1	Eosin Y	CH₂Cl₂	72	0
2	Rose Bengal	CH₂Cl₂	39	0
3	4CzIPN	CH₂Cl₂	70	0
4	—	CH₂Cl₂	74	0
5	—	DMF	0	0
6	—	DMSO	0	0
7	—	CH₃CN	48	0
8	—	DCE	33	0
9	—	CHCl₃	26	0
10	—	Acetone	43	0
11	—	AcOEt	38	0
12	—	1,4-Dioxane	76	0
13	—	THF	0	98
14	—	1,4-Dioxane	15^c	0
15	—	1,4-Dioxane	10^d	0
16	—	1,4-Dioxane	18^e	0
17	—	1,4-Dioxane	0^f	0
18	—	THF	0	0^f

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

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

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