高 N2 选择性钯催化 1,2,3-三唑芳基化反应。
Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.
机构信息
Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Sep 12;50(38):8944-7. doi: 10.1002/anie.201103882. Epub 2011 Aug 18.
Abstract
[Image: see text] Highly -selective arylation of 4,5-unsubstituted and 4-substituted 1,2,3-triazoles was achieved for the first time by Pd/ catalyst system. A wide range of -aryl-1,2,3-triazoles were prepared from aryl bromides, chlorides and triflates with excellent (95–99%) -selectivity. DFT calculations suggest that formation of -arylated 1,2,3-triazoles is favored kinetically.
摘要
[图像：见文本] 通过 Pd/催化剂体系，首次实现了对 4,5-未取代和 4-取代的 1,2,3-三唑的高选择性芳基化。通过芳基溴化物、氯化物和三氟甲磺酸酯，制备了一系列具有优异的（95-99%）-选择性的-芳基-1,2,3-三唑。DFT 计算表明，-芳基化 1,2,3-三唑的形成在动力学上是有利的。
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7
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Chem Commun (Camb). 2008 Jul 28(28):3254-6. doi: 10.1039/b805328f. Epub 2008 Jun 2.
8
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10
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