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蓝光LED照射下氮丙啶和咪唑烷骨架的发散性合成

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation.

作者信息

Cheng Xiao, Cai Bao-Gui, Mao Hui, Lu Juan, Li Lei, Wang Kun, Xuan Jun

机构信息

Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, People's Republic of China.

Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University), Ministry of Education, Hefei 230601, People's Republic of China.

出版信息

Org Lett. 2021 Jun 4;23(11):4109-4114. doi: 10.1021/acs.orglett.1c00979. Epub 2021 May 14.

DOI:10.1021/acs.orglett.1c00979
PMID:33989004
Abstract

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.

摘要

我们开发了一种可见光促进的α-重氮酯与六氢-1,3,5-三嗪的发散环加成反应,通过简单地改变所用的反应介质,以平均良好的产率得到了一系列氮丙啶和咪唑烷骨架。值得注意的是,该反应在仅可见光照射下发生,无需外源光氧化还原催化剂。更重要的是,基于对照实验和密度泛函理论计算结果提出了合理的反应机理。

相似文献

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Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation.蓝光LED照射下氮丙啶和咪唑烷骨架的发散性合成
Org Lett. 2021 Jun 4;23(11):4109-4114. doi: 10.1021/acs.orglett.1c00979. Epub 2021 May 14.
2
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Copper-catalyzed reaction of aziridine for the synthesis of substituted imidazolidine and imidazolidinone.用于合成取代咪唑烷和咪唑烷酮的氮丙啶的铜催化反应。
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引用本文的文献

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Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.用于合成含氮杂环骨架的无金属催化剂的最新进展:聚焦于五元环和六元环的综述
RSC Adv. 2025 Mar 31;15(13):9676-9755. doi: 10.1039/d5ra00962f. eCollection 2025 Mar 28.
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Recent advances in the synthesis of highly substituted imidazolidines.高度取代咪唑烷合成的最新进展。
RSC Adv. 2024 Sep 26;14(42):30758-30806. doi: 10.1039/d4ra06010e. eCollection 2024 Sep 24.
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The efficient synthesis of three-membered rings photo- and electrochemical strategies.
三元环的高效合成:光化学和电化学策略。
Chem Sci. 2024 Aug 14;15(34):13576-604. doi: 10.1039/d4sc02512a.
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Visible-light-induced organocatalytic enantioselective N-H insertion of α-diazoesters enabled by indirect free carbene capture.间接游离卡宾捕获实现可见光诱导的有机催化α-重氮酯对映选择性N-H插入反应
Chem Sci. 2022 Nov 29;14(4):843-848. doi: 10.1039/d2sc05149d. eCollection 2023 Jan 25.