Optimization of the Conditions for Copper‐Mediated N‐Arylation of Heteroarylamines

作者: Yifeng Liu , Yajun Bai , Juan Zhang , Yangyang Li , Junping Jiao

DOI: 10.1002/EJOC.200700577

关键词: CopperCatalysisChemistryCoupling reactionArylNucleophileLigandOrganic chemistrySolventPolymer chemistryBase (chemistry)

摘要: Simple and inexpensive copper-mediated N-arylation ofheteroarylamines was achieved by using N,N′-dimethylethylenediamine as a ligand K2CO3 base in dioxane heated at 100 °C. In this coupling reaction, the influence of copper species, ligand, solvent investigated detail. N-Arylated derivatives several heteroarylamines were synthesized under optimized reaction conditions, all products isolated good yields. By controlling amount CuI/DMEDA added, with weak nucleophilic activity coupled aryl iodides or bromides. The catalyst for C–N bond-forming follows order CuI > Cu0 > CuII. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

参考文章(52)
Fuk Yee Kwong, Stephen L. Buchwald, Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines. Organic Letters. ,vol. 5, pp. 793- 796 ,(2003) , 10.1021/OL0273396
Nandkumar M. Patil, Ashutosh A. Kelkar, Raghunath V. Chaudhari, Synthesis of triarylamines by copper-catalyzed amination of aryl halides Journal of Molecular Catalysis A: Chemical. ,vol. 223, pp. 45- 50 ,(2004) , 10.1016/J.MOLCATA.2003.09.038
Shinya Usui, Takayoshi Suzuki, Yoshifumi Hattori, Kazuma Etoh, Hiroki Fujieda, Makoto Nishizuka, Masayoshi Imagawa, Hidehiko Nakagawa, Kohfuku Kohda, Naoki Miyata, Design, synthesis, and biological activity of novel PPARγ ligands based on rosiglitazone and 15d-PGJ2 Bioorganic & Medicinal Chemistry Letters. ,vol. 15, pp. 1547- 1551 ,(2005) , 10.1016/J.BMCL.2005.01.074
Artis Klapars, Xiaohua Huang, Stephen L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides. Journal of the American Chemical Society. ,vol. 124, pp. 7421- 7428 ,(2002) , 10.1021/JA0260465
Lee A McDermott, Mary Simcox, Brian Higgins, Tom Nevins, Kenneth Kolinsky, Melissa Smith, Hong Yang, Jia K Li, Yingsi Chen, June Ke, Navita Mallalieu, Tom Egan, Stan Kolis, Aruna Railkar, Louise Gerber, Kin-Chun Luk, None, RO4383596, an orally active KDR, FGFR, and PDGFR inhibitor: synthesis and biological evaluation. Bioorganic & Medicinal Chemistry. ,vol. 13, pp. 4835- 4841 ,(2005) , 10.1016/J.BMC.2005.05.012
Brian A Johns, Kristjan S Gudmundsson, Elizabeth M Turner, Scott H Allen, David K Jung, Connie J Sexton, F.Leslie Boyd, Michael R Peel, Pyrazolo[1,5-a]pyridines: synthetic approaches to a novel class of antiherpetics Tetrahedron. ,vol. 59, pp. 9001- 9011 ,(2003) , 10.1016/J.TET.2003.02.003
John F. Hartwig, Motoi Kawatsura, Sheila I. Hauck, Kevin H. Shaughnessy, Luis M. Alcazar-Roman, Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C−N Bond Formation with a Commercial Ligand Journal of Organic Chemistry. ,vol. 64, pp. 5575- 5580 ,(1999) , 10.1021/JO990408I
Francis X. Tavares, Joyce A. Boucheron, Scott H. Dickerson, Robert J. Griffin, Frank Preugschat, Stephen A. Thomson, Tony Y. Wang, Hui-Qiang Zhou, N-Phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy. Journal of Medicinal Chemistry. ,vol. 47, pp. 4716- 4730 ,(2004) , 10.1021/JM040063I
Dawei Ma, Yongda Zhang, Jiangchao Yao, Shihui Wu, Fenggang Tao, Accelerating effect induced by the structure of αamino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzolactam-V8 Journal of the American Chemical Society. ,vol. 120, pp. 12459- 12467 ,(1998) , 10.1021/JA981662F
Scott N. VanderWel, Patricia J. Harvey, Dennis J. McNamara, Joseph T. Repine, Paul R. Keller, John Quin, R. John Booth, William L. Elliott, Ellen M. Dobrusin, David W. Fry, Peter L. Toogood, Pyrido[2,3-d]pyrimidin-7-ones as specific inhibitors of cyclin-dependent kinase 4. Journal of Medicinal Chemistry. ,vol. 48, pp. 2371- 2387 ,(2005) , 10.1021/JM049355+