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乙烯基醚的催化分子间氢胺化反应。

Catalytic intermolecular hydroamination of vinyl ethers.

作者信息

Pahadi Nirmal K, Tunge Jon A

机构信息

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045-7582.

出版信息

Synlett. 2009 Dec 1;19:3135-3138. doi: 10.1055/s-0029-1218293.

DOI:10.1055/s-0029-1218293
PMID:20523749
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2879649/
Abstract

This manuscript details the development of a palladium-catalyzed hydroamination of vinyl ethers. It is proposed that palladium catalyzes the hydroamination via Bronsted base catalysis, where palladium is protonated by the relatively acidic sulfonamide to generate a palladium hydride as well as the active anionic sulfonamide nucleophile. Thus, this process is distinct from known palladium-catalyzed hydroaminations of styrene derivatives that utilize less acidic amines.

摘要

本手稿详细介绍了钯催化乙烯基醚的氢胺化反应的发展情况。有人提出,钯通过布朗斯特碱催化氢胺化反应,其中钯被相对酸性的磺酰胺质子化,生成氢化钯以及活性阴离子磺酰胺亲核试剂。因此,该过程不同于已知的利用酸性较弱的胺进行的钯催化苯乙烯衍生物的氢胺化反应。

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本文引用的文献

1
Cu(I)-catalyzed intramolecular hydroamination of unactivated alkenes bearing a primary or secondary amino group in alcoholic solvents.在醇类溶剂中,铜(I)催化带有伯氨基或仲氨基的未活化烯烃的分子内氢胺化反应。
Org Lett. 2009 May 21;11(10):2145-7. doi: 10.1021/ol9007712.
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Intramolecular hydroamination of unactivated alkenes with secondary alkyl- and arylamines employing [Ir(COD)Cl]2 as a catalyst precursor.以[Ir(COD)Cl]2作为催化剂前体,实现未活化烯烃与仲烷基胺和芳基胺的分子内氢胺化反应。
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Hydroamination: direct addition of amines to alkenes and alkynes.氢胺化反应:胺类直接加成到烯烃和炔烃上。
Chem Rev. 2008 Sep;108(9):3795-892. doi: 10.1021/cr0306788. Epub 2008 Aug 26.
4
Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity.双环烯烃和二烯的分子间催化不对称氢胺化反应,产率高且对映选择性好。
J Am Chem Soc. 2008 Sep 17;130(37):12220-1. doi: 10.1021/ja803523z. Epub 2008 Aug 21.
5
(Triphenyl phosphite)gold(I)-catalyzed intermolecular hydroamination of alkenes and 1,3-dienes.(亚磷酸三苯酯)金(I)催化的烯烃和1,3 - 二烯的分子间氢胺化反应
Org Lett. 2008 Jul 17;10(14):2919-22. doi: 10.1021/ol801104w. Epub 2008 Jun 14.
6
Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: the difference between Brønsted and Lewis acid catalysis.硝酮与乙烯基乙醚的对映选择性1,3-偶极环加成反应:布朗斯特酸和路易斯酸催化的差异
Angew Chem Int Ed Engl. 2008;47(13):2411-3. doi: 10.1002/anie.200705314.
7
Mechanistic studies of a palladium-catalyzed intramolecular hydroamination of unactivated alkenes: protonolysis of a stable palladium alkyl complex is the turnover-limiting step.钯催化未活化烯烃分子内氢胺化反应的机理研究:稳定钯烷基配合物的质子解是周转限制步骤。
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8
Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.温和条件下,铑催化未活化的末端烯烃和内烯烃与伯胺和仲胺进行分子内氢胺化反应。
J Am Chem Soc. 2008 Feb 6;130(5):1570-1. doi: 10.1021/ja710126x. Epub 2008 Jan 10.
9
Efficient C-N bond formations catalyzed by a proton-exchanged montmorillonite as a heterogeneous Brønsted acid.质子交换蒙脱石作为非均相布朗斯特酸催化的高效C-N键形成反应。
Org Lett. 2006 Sep 28;8(20):4617-20. doi: 10.1021/ol0619821.
10
Copolymerization of silyl vinyl ethers with olefins by (alpha-diimine)PdR+.(α-二亚胺)钯正离子催化硅烷基乙烯基醚与烯烃的共聚反应
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