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Pure Appl. Chem., 2004, Vol. 76, No. 9, pp. 1605-1619

http://dx.doi.org/10.1351/pac200476091605

Palladium-catalyzed arylation of linear and cyclic polyamines

I. P. Beletskaya and A. D. Averin

Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, Moscow 119992, Russia

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  • Huang Pei, Wang Yi-Xiang, Yu Hong-Fei, Lu Jian-Mei: N-Heterocyclic Carbene–Palladium(II)–4,5-Dihydrooxazole Complexes: Synthesis and Catalytic Activity toward Amination of Aryl Chlorides. Organometallics 2014, 33, 1587. <http://dx.doi.org/10.1021/om401028d>
  • Toulot Stéphanie, Heinrich Timo, Leroux Frédéric R.: Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed versus Copper-Catalyzed Aminations of Halothiazoles. Adv. Synth. Catal. 2013, 355, 3263. <http://dx.doi.org/10.1002/adsc.201300591>
  • Zhu Lei, Ye Yue-Mei, Shao Li-Xiong: Well-defined NHC–Pd(II)–Im (NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C–N coupling of primary amines with aryl chlorides. Tedrahedron 2012, 68, 2414. <http://dx.doi.org/10.1016/j.tet.2012.01.008>
  • Anderson James C., Noble Adam, Tocher Derek A.: Reductive Nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing Indolines and Tetrahydroquinolines. J. Org. Chem. 2012, 77, 6703. <http://dx.doi.org/10.1021/jo3010827>
  • Lü Bo, Li Pengbin, Fu Chunling, Xue Liqin, Lin Zhenyang, Ma Shengming: 2,6-Diisopropoxyphenyl(dicyclohexyl)phosphine: A New Ligand for Palladium-Catalyzed Amination Reactions of Aryl Chlorides with Potassium Hydroxide as the Base. Synth Catal 2011, 353, 100. <http://dx.doi.org/10.1002/adsc.201000349>
  • Surry David S., Buchwald Stephen L.: Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide. Chem Sci 2011, 2, 27. <http://dx.doi.org/10.1039/c0sc00331j>
  • Doherty Simon, Knight Julian G., McGrady John P., Ferguson Alexandra M., Ward Nicholas A. B., Harrington Ross W., Clegg William: ortho,ortho′-Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium-Catalyzed CC and CN Bond Formation. Adv Synth Catal 2010, 352, 201. <http://dx.doi.org/10.1002/adsc.200900577>
  • Bouteiller Cédric, Becerril-Ortega Javier, Marchand Patrice, Nicole Olivier, Barré Louisa, Buisson Alain, Perrio Cécile: Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil. Org Biomol Chem 2010, 8, 1111. <http://dx.doi.org/10.1039/b923255a>
  • Surry David S., Buchwald Stephen L.: Biarylphosphanliganden in der palladiumkatalysierten Aminierung. Angew Chem 2008, 120, 6438. <http://dx.doi.org/10.1002/ange.200800497>
  • Surry David S., Buchwald Stephen L.: Biaryl Phosphane Ligands in Palladium-Catalyzed Amination. Angew Chem Int Ed 2008, 47, 6338. <http://dx.doi.org/10.1002/anie.200800497>
  • Biscoe Mark R., Barder Timothy E., Buchwald Stephen L.: Electronic Effects on the Selectivity of Pd-Catalyzed CN Bond-Forming Reactions Using Biarylphosphine Ligands: The Competitive Roles of Amine Binding and Acidity. Angew Chem 2007, 119, 7370. <http://dx.doi.org/10.1002/ange.200702122>
  • Biscoe Mark R., Barder Timothy E., Buchwald Stephen L.: Electronic Effects on the Selectivity of Pd-Catalyzed CN Bond-Forming Reactions Using Biarylphosphine Ligands: The Competitive Roles of Amine Binding and Acidity. Angew Chem Int Ed 2007, 46, 7232. <http://dx.doi.org/10.1002/anie.200702122>
  • Beletskaya Irina P., Averin Alexey D.: Palladium-Catalyzed Arylation of Linear and Cyclic Polyamines. ChemInform 2005, 36. <http://dx.doi.org/10.1002/chin.200509273>