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钯催化的硝基芳烃的芳基化和苄基化反应:使用芳基磺酸盐和苄基醋酸盐。

Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates.

机构信息

St. Olaf College , 1520 St. Olaf Avenue, Northfield, Minnesota 55057, United States.

出版信息

J Org Chem. 2017 Jul 7;82(13):6946-6957. doi: 10.1021/acs.joc.7b00550. Epub 2017 Jun 15.

DOI:10.1021/acs.joc.7b00550
PMID:28617611
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5679234/
Abstract

Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenzene is also reported. The relative rate for the arylation of halides is greater than that of tosylates using the reported reaction parameters. These studies enhance the scope of electrophiles for nitroarene arylations and benzylations, which was hitherto limited to the use of halide electrophiles.

摘要

本文描述了使用芳基磺酸盐或苄基醋酸盐的 Pd 催化的硝基唑的芳基化或苄基化反应。电子变化的芳基对甲苯磺酸盐和甲磺酸盐以及苄基醋酸盐提供了芳基化和苄基化产物。还报道了硝基苯的芳基化。在报道的反应条件下,卤化物的芳基化相对速率大于对甲苯磺酸盐的芳基化相对速率。这些研究扩展了用于硝基芳烃芳基化和苄基化的亲电试剂的范围,此前仅限于使用卤代亲电试剂。

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本文引用的文献

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Tetrahedron. 2017 Apr 20;73(16):2196-2209. doi: 10.1016/j.tet.2017.02.021. Epub 2017 Feb 14.
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Dual gold photoredox C(sp(2))-C(sp(2)) cross couplings - development and mechanistic studies.双金光氧化还原C(sp(2))-C(sp(2))交叉偶联反应——方法开发与机理研究
Chem Commun (Camb). 2016 Aug 9;52(66):10163-6. doi: 10.1039/c6cc05078f.
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Cross-Couplings Using Aryl Ethers via C-O Bond Activation Enabled by Nickel Catalysts.镍催化剂促进的通过 C-O 键活化的芳基醚的交叉偶联反应。
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Nickel complexes for catalytic C-H bond functionalization.
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Catalytic C-H allylation and benzylation of pyrazoles.吡唑的催化C-H烯丙基化和苄基化反应
J Org Chem. 2015 Jan 2;80(1):690-7. doi: 10.1021/jo5025317. Epub 2014 Dec 17.
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Synthesis of extended π-systems through C-H activation.通过 C-H 活化合成扩展的π-体系。
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8
Palladium-Catalyzed Intra- and Intermolecular C-H Arylation Using Mesylates: Synthetic Scope and Mechanistic Studies.使用甲磺酸盐的钯催化分子内和分子间C-H芳基化:合成范围与机理研究
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Regioselective and guided C-H activation of 4-nitropyrazoles.4-硝基吡唑的区域选择性和导向C-H活化
J Org Chem. 2014 Apr 4;79(7):2906-15. doi: 10.1021/jo4025418. Epub 2014 Mar 24.