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协同亲核芳香取代反应

Concerted Nucleophilic Aromatic Substitution Reactions.

作者信息

Rohrbach Simon, Smith Andrew J, Pang Jia Hao, Poole Darren L, Tuttle Tell, Chiba Shunsuke, Murphy John A

机构信息

Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.

出版信息

Angew Chem Int Ed Engl. 2019 Nov 11;58(46):16368-16388. doi: 10.1002/anie.201902216. Epub 2019 Sep 13.

DOI:10.1002/anie.201902216
PMID:30990931
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6899550/
Abstract

Recent developments in experimental and computational chemistry have identified a rapidly growing class of nucleophilic aromatic substitutions that proceed by concerted (cS Ar) rather than classical, two-step, S Ar mechanisms. Whereas traditional S Ar reactions require substantial activation of the aromatic ring by electron-withdrawing substituents, such activating groups are not mandatory in the concerted pathways.

摘要

实验化学和计算化学方面的最新进展已经确定了一类快速发展的亲核芳香取代反应,这些反应是通过协同(cS Ar)而非经典的两步S Ar机制进行的。传统的S Ar反应需要吸电子取代基对芳香环进行大量活化,而在协同反应途径中,此类活化基团并非必需。

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8
Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.碘代芳烃的活化:向绿色可持续转化迈进一大步。
Chem Rev. 2025 Mar 26;125(6):3440-3550. doi: 10.1021/acs.chemrev.4c00808. Epub 2025 Mar 7.
9
Photoredox-Catalyzed Nucleophilic Aromatic Substitution of Halophenols with Azoles via Oligomeric Phenylene Oxide Radicals.通过低聚亚苯基氧化物自由基实现的光氧化还原催化卤代酚与唑类的亲核芳香取代反应。
J Am Chem Soc. 2025 Mar 19;147(11):9931-9938. doi: 10.1021/jacs.5c01012. Epub 2025 Mar 6.
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Development of a Thioetherification of Heteroarene Electrophiles with Broad Scope via a Proton Transfer Dual Ionization Mechanism.通过质子转移双电离机制实现具有广泛底物范围的杂芳烃亲电试剂的硫醚化反应的开发。
J Am Chem Soc. 2025 Feb 13. doi: 10.1021/jacs.4c18304.
用双金属亲核试剂阐明亲核芳香取代反应途径。
Chem Commun (Camb). 2019 Feb 5;55(12):1805-1808. doi: 10.1039/c8cc09701a.
4
Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids.α-氨基酸的不对称和几何选择性 α-烯丙基化反应。
Angew Chem Int Ed Engl. 2019 Feb 18;58(8):2418-2422. doi: 10.1002/anie.201813984. Epub 2019 Jan 31.
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Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles.酮的室温无过渡金属分子内α-芳基化反应:一种温和合成四环吲哚和7-氮杂吲哚的方法
Org Lett. 2019 Jan 4;21(1):320-324. doi: 10.1021/acs.orglett.8b03831. Epub 2018 Dec 21.
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Base-Mediated Defluorosilylation of C(sp )-F and C(sp )-F Bonds.碱介导的C(sp³)-F键和C(sp²)-F键的脱氟硅基化反应
Angew Chem Int Ed Engl. 2019 Feb 11;58(7):2064-2068. doi: 10.1002/anie.201813294. Epub 2019 Jan 17.
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An Electrocatalytic Newman-Kwart-type Rearrangement.一种电催化的纽曼-夸特型重排反应。
Org Lett. 2018 Dec 7;20(23):7483-7487. doi: 10.1021/acs.orglett.8b03257. Epub 2018 Nov 29.
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Silyldefluorination of Fluoroarenes by Concerted Nucleophilic Aromatic Substitution.通过协同亲核芳香取代实现氟代芳烃的硅基脱氟反应
Angew Chem Int Ed Engl. 2019 Jan 2;58(1):283-287. doi: 10.1002/anie.201808646. Epub 2018 Dec 3.
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Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds.基于 Aryne 的策略在天然多环化合物全合成中的应用。
Chem Soc Rev. 2018 Oct 29;47(21):8030-8056. doi: 10.1039/c8cs00350e.
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Meisenheimer Complexes in S Ar Reactions: Intermediates or Transition States?S Ar反应中的迈森海默络合物:中间体还是过渡态?
Angew Chem Int Ed Engl. 2018 Nov 5;57(45):14686-14688. doi: 10.1002/anie.201809606. Epub 2018 Oct 15.