钯催化的芳基氯代吲哚、吡咯和呋喃芳基化反应。
Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.
机构信息
Department of Chemistry, University of Houston, Houston, Texas 77204, United States.
出版信息
J Org Chem. 2011 Jan 21;76(2):471-83. doi: 10.1021/jo1018969. Epub 2010 Dec 30.
Abstract
The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.
摘要
钯催化的吲哚、吡咯和呋喃的芳基氯化直接芳基化已被证明。该方法采用醋酸钯催化剂、2-(二环己基膦基)联苯配体和无机碱。富电子和缺电子的芳基氯化物以及氯吡啶偶联伙伴都可以使用，并且得到的芳基化杂环化合物产率中等至良好。为了达到最佳效果，需要对碱、配体和溶剂进行优化。
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2
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Angew Chem Int Ed Engl. 2010 Apr 1;49(15):2768-71. doi: 10.1002/anie.200906921.
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Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2202-5. doi: 10.1002/anie.200906996.
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J Org Chem. 2010 Mar 5;75(5):1550-60. doi: 10.1021/jo9022793.
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J Am Chem Soc. 2010 Feb 17;132(6):1822-4. doi: 10.1021/ja909807f.
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