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有机合成中的乙烯基叠氮化物：综述

Vinyl azides in organic synthesis: an overview.

作者信息

Gholami Fateme, Yousefnejad Faeze, Larijani Bagher, Mahdavi Mohammad

机构信息

School of Chemistry, College of Science, University of Tehran Tehran Iran.

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences Tehran Iran

出版信息

RSC Adv. 2023 Jan 4;13(2):990-1018. doi: 10.1039/d2ra06726a. eCollection 2023 Jan 3.

DOI:10.1039/d2ra06726a
PMID:36686934
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9811501/
Abstract

Among organic azides, vinyl azides have attracted significant attention, because of their unique properties in organic synthesis, which led to reports of many types of research on this versatile conjugated azide in recent years. This magical precursor can also be converted into intermediates such as iminyl radicals, 2-azirines, iminyl metal complexes, nitrilium ions, and iminyl ions, making this compound useful in heterocycle synthesis.

摘要

在有机叠氮化物中，乙烯基叠氮化物因其在有机合成中的独特性质而备受关注，这导致近年来有许多关于这种多功能共轭叠氮化物的各类研究报道。这种神奇的前体还可以转化为亚胺基自由基、2-氮杂环丙烷、亚胺基金属配合物、亚胺鎓离子和亚胺离子等中间体，使得该化合物在杂环合成中很有用。

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Org Biomol Chem. 2022 May 18;20(19):3907-3912. doi: 10.1039/d2ob00458e.
2
CuCl·2HO/TBHP mediated synthesis of β-enaminones coupling reaction of vinyl azides with aldehydes.CuCl·2HO/TBHP 介导的β-烯胺酮合成——叠氮乙烯与醛的偶联反应。
Org Biomol Chem. 2022 Mar 2;20(9):1952-1957. doi: 10.1039/d1ob02479e.
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Pd(II)-Catalyzed Synthesis of Alicyclic[]-Fused Pyridines via C(sp)-H Activation of -Unsaturated -Acetyl Hydrazones with Vinyl Azides.
Cluster model study of the mechanism and origins of enantio- and chemoselectivity in non-heme iron enzyme-catalyzed C-H azidation.
非血红素铁酶催化C-H叠氮化反应中对映选择性和化学选择性的机理及起源的簇模型研究
RSC Adv. 2025 Mar 24;15(12):8931-8937. doi: 10.1039/d5ra00632e. eCollection 2025 Mar 21.
钯（II）催化通过 C(sp)-H 活化 -不饱和 -乙酰腙与乙烯基叠氮化物合成脂环[ ]稠合吡啶。
J Org Chem. 2022 Jan 7;87(1):159-171. doi: 10.1021/acs.joc.1c02086. Epub 2021 Dec 21.
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An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives.芳基硫醇-乙烯基叠氮化物偶联反应和硫醇-乙烯基叠氮化物偶联/环化串联反应：β-酮亚砜和芳基并 5-亚甲基-2-吡咯烷酮衍生物的高效合成。
Org Biomol Chem. 2021 Jun 16;19(23):5169-5176. doi: 10.1039/d1ob00328c.
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Regioselective Synthesis of 2,4-Diaryl-6-trifluoromethylated Pyridines through Copper-Catalyzed Cyclization of CF-Ynones and Vinyl Azides.通过铜催化的 CF-炔酮和乙烯基叠氮化物的环化反应，区域选择性合成 2,4-二芳基-6-三氟甲基化吡啶。
J Org Chem. 2021 May 7;86(9):6423-6432. doi: 10.1021/acs.joc.1c00275. Epub 2021 Apr 27.
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Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions.α-脒基酮的合成通过在无催化剂条件下羧酸与乙烯基叠氮化物的级联反应。
J Org Chem. 2020 Nov 6;85(21):13710-13720. doi: 10.1021/acs.joc.0c01871. Epub 2020 Oct 28.
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Iridium-Catalyzed Enantioselective α-Allylic Alkylation of Amides Using Vinyl Azide as Amide Enolate Surrogate.铱催化的酰胺作为酰胺烯醇化物替代物的对映选择性α-烯丙基烷基化反应。
Org Lett. 2020 Oct 2;22(19):7752-7756. doi: 10.1021/acs.orglett.0c03002. Epub 2020 Sep 16.
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Indium(III) Catalyzed Reactions of Vinyl Azides and Indoles.铟（III）催化的叠氮乙烯与吲哚的反应。
Org Lett. 2020 May 15;22(10):3759-3764. doi: 10.1021/acs.orglett.0c00919. Epub 2020 Apr 24.
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BF·OEt-Catalyzed Vinyl Azide Addition to in Situ Generated -Acyl Iminium Salts: Synthesis of 3-Oxoisoindoline-1-acetamides.BF·OEt催化乙烯基叠氮化物加成到原位生成的-酰基亚胺盐：3-氧代异吲哚啉-1-乙酰胺的合成。
J Org Chem. 2019 Dec 20;84(24):15865-15876. doi: 10.1021/acs.joc.9b02127. Epub 2019 Nov 27.
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Visible Light Photoredox-Catalyzed α-Alkylation of Cyclic Tertiary Arylamines.可见光光氧化还原催化环状叔芳基胺的α-烷基化反应。
J Org Chem. 2019 Nov 15;84(22):14760-14769. doi: 10.1021/acs.joc.9b02347. Epub 2019 Oct 31.