Palladium-catalyzed cross-coupling of electron-deficient heteroaromatic amines with heteroaryl halides

Synthetic Communications

Volumn 43, Issue 3, 2013, Pages 456-463

  Zhang, Gang ^a   Wang, Xiaojian ^a   Li, Chun ^a   Yin, Dali ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Buchwald Hartwig reaction; heteroaromatic amines; heteroaryl halides; Pd catalyzed cross coupling

Indexed keywords

AMINE; FERROCENE DERIVATIVE; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84868618674     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.603068     Document Type: Article

References (18)

1. (a) Hughes, C. C.; Fenical, W. Total synthesis of the ammosamides. J. Am. Chem. Soc. 2010, 132, 2528-2529;
2. (b) Reddy, P. V.; Banerjee, B.; Cushman, M. Efficient total synthesis of ammosamide B. Org. Lett. 2010, 12, 3112-3114.
3. Yuan, L.; Sumpter, B. G.; Abboud, K. A.; Castellano, R. K. Links between through-bond interactions and assembly structure in simple piperidones. New J. Chem. 2008, 32, 1924-1934.
4. (a) Eelkema, R.; Anderson, H. L. Synthesis of end-functionalized polyanilines. Macro-molecules 2008, 41, 9930-9933;
5. (b) Surry, D. S.; Buchwald, S. L. Selective palladium-catalyzed arylation of ammonia: Synthesis of anilines as well as symmetrical and unsymmetrical di-and triarylamines. J. Am. Chem. Soc. 2007, 129, 10354-10355. (Pubitemid 47330251)
6. (a) Henderson, J. L.; McDermott, S. M.; Buchwald, S. L. Palladium-catalyzed amination of unprotected halo-7-azaindoles. Org. Lett. 2010, 12, 4438-4441;
7. (b) Hartwig, J. F. Carbon-heteroatom bond formation catalysed by organometallic complexes. Nature 2008, 455, 314-322.
8. Christmann, U.; Vilar, R. Monoligated palladium species as catalysts in cross-coupling reactions. Angew. Chem., Int. Ed. Engl. 2005, 44, 366-374. (Pubitemid 40138339)
9. (a) Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Pd-catalyzed N-arylation of heteroarylamines. Org. Lett. 2002, 4, 3481-3484;
10. (b) Schulte, J. P.; Tweedie, S. R. Palladium-catalyzed couplings of heteroaryl amines with aryl halides using sodium phenolate as the stoichiometric base. Synlett. 2007, 18, 2331-2336. (Pubitemid 47521990)
11. Ahrendt, K. A.; Buckmelter, A. J.; Feng, B.; Grina, J.; Hansen, J. D.; Laird, E. R.; Malesky, K.; Mathieu, S.; Moreno, D. A.; Newhouse, B.; Ren, L.; Rudolph, J.; Wenglowsky, S. M.; Wen, Z.; Young, W. B. N-(6-Aminopyridin-3-yl)-3- (sulfonamido) benzamide derivatives as B-RAF inhibitors for the treatment of cancer WO Patent 2009111280-A1, September 11, 2009.
12. Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems. J. Org. Chem. 2001, 66, 7729-7737. (Pubitemid 33063968)
13. Smith, W.; Sawyer, J. An SnAr-based preparation of 1-(2-, 3-, and 4-pyridyl) indoles using potassium fluoride/alumina. Heterocycles 1999, 51, 157-160.
14. Yadav, V.; Ganesh Babu, K.; Mittal, M. KF-Al2O3 is an efficient solid support reagent for the acetylation of amines, alcohols, and phenols: Impeding effect of solvent on the reaction rate. Tetrahedron 2001, 57, 7047-7051. (Pubitemid 32722026)
15. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. A simple catalytic method for the conversion of aryl bromides to arylamines. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
16. Tietze, M.; Iglesias, A.; Merisor, E.; Conrad, J.; Klaiber, I.; Beifuss, U. Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides. Org. Lett. 2005, 7, 1549-1552. (Pubitemid 40585928)
17. (a) Roy, S.; Westmaas, J. A.; Buda, F.; Reedijk, J. Platinum(II) compounds with chelating ligands based on pyridine and pyrimidine: Synthesis, characterizations, DFT calculations, cytotoxic assays and binding to a DNA model base. J. Inorg. Biochem. 2009, 103, 1278-1287;
18. (b) Bock, H.; Schödel, H.; Näther, C.; Butenschön, F. Wechselwirkungen in Kristallen, 110: Mitteilung, Die Dimorphic von (2-Pyridyl)(2-pyrimidyl)amin. Helv. Chim. Acta 1997, 80, 593.