Highly efficient and reusable copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides

Molecules

Volumn 14, Issue 12, 2009, Pages 5169-5178

  Kim, A Young ^a   Lee, Hyun Ju ^a   Park, Ji Chan ^b   Kang, Hyunju ^a   Yang, Haesik ^a   Song, Hyunjoon ^a   Park, Kang Hyun ^a  

^a Pusan National University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

Acetylene black; Copper; Heterocycles; Heterogeneous catalyst; N arylation

Indexed keywords

COPPER; HALOGEN; HETEROCYCLIC COMPOUND; NITROGEN;

ARTICLE; CATALYSIS; CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

CATALYSIS; COPPER; HALOGENS; HETEROCYCLIC COMPOUNDS; MICROSCOPY, ELECTRON, TRANSMISSION; NITROGEN; X-RAY DIFFRACTION;

EID: 73849125965     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14125169     Document Type: Article

References (28)

1. Craig, P.N. In Comprehensive Medicinal Chemistry; Drayton, C.J., Ed.; Pergamon Press: New York, NY, USA, 1991; Vol., 8.
2. 2+ antagonism and thromboxane A2 synthase inhibition. J. Med. Chem. 1993, 36, 2964-2972.
3. Negwer, M. Organic-Chemical Drugs and Their SYNONYMS: An International Survey, 7th ed.; Akademie Verlag GmbH: Berlin, Germany, 1994.
4. Kundu, N.G.; Mahanty, J.S.; Chowdhurry, C.; Dasgupta, S.K.; Das, B.; Spears, C.P.; Balzarini, J.; De Clercq, E. Studies on uracil derivatives and analogs., 25 5-(acylethynyl)uracils, 5-(acylethynyl)-2′-deoxyuridines and 5-(acylethynyl)-1-(2-hydroxyethoxy)methyluracils. their synthesis, antiviral and cytotoxic activities. Eur. J. Med. Chem. 1999, 34, 389-398.
5. Kunz, K.; Scholtz, U.; Ganzer, D. Renaissance of Ullmann and Goldberg reactions - Progress in copper catalyzed C-N-, C-O- and C-S-coupling. Synlett 2003, 15, 2428-2439.
6. Herrmann, W.A. N-heterocyclic carbenes. Part, 31N-heterocyclic carbenes: A new concept in organometallic catalysis. Angew. Chem. Int. Ed. 2002, 41, 1290-1309.
7. Ley, S.V.; Thomas, A.W. Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation. Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
8. Beletskaya, I.P.; Cheprakov, A.V. Copper in cross-coupling reactions. Coord. Chem. Rev. 2004, 248, 2337-2364.
9. Corbet, J.P.; Mignani, G. Selected Patented Cross-Coupling Reaction Technologies. Chem. Rev. 2006, 106, 2651-2710.
10. Altman, R.A.; Shafir, A.; Lichtor, P.A.; Buchwald, S.L. An Improved Cu-Based Catalyst System for the Reactions of Alcohols with Aryl Halides. J. Org. Chem. 2008, 73, 284-286.
11. Chen, Y.J.; Chen, H.H. 1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols. Org. Lett. 2006, 8, 5609-5612.
12. Ma, D.; Cai, Q. N, N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides. Org. Lett. 2003, 5, 3799-3802.
13. Cristau, H.J.; Cellier, P.P.; Hamada, S.; Spindler, J.F.; Taillefer, M. A general and mild ullmann-type synthesis of diaryl ethers. Org. Lett. 2004, 6, 913-916.
14. Kwong, F.Y.; Klapars, A.; Buchwald, S.L. Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere. Org. Lett. 2002, 4, 581-584.
15. Wolf, C.; Liu, S.; Mei, X.; August, A.T.; Casimir, M.D. Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines. J. Org. Chem. 2006, 71, 3270-3273.
16. Pan, Y.; Lu, H.; Fang, Y.; Fang, X.; Chen, L.; Qian, J.; Wang, J.; Li, C. Synthesis of pyrroles via copper-catalyzed coupling of amines with bromoenones. Synthesis 2007, 1242-1246.
17. Fang, Y.; Li, C. Preference of 4-exo Ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols. J. Am. Chem. Soc. 2007, 129, 8092-8093.
18. Lipshutz, B.H.; Unger, J.B.; Taft, B.R. Copper-in-charcoal (cu/c) promoted diaryl ether formation. Org. Lett. 2007, 9, 1089-1092.
19. Goodbrand, H.B.; Hu, N.X. Ligand-Accelerated catalysis of the ullmann condensation: Application to hole conducting triarylamines. J. Org. Chem. 1999, 64, 670-674.
20. Fagan, P.J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A.J. Using intelligent/random library screening to design focused libraries for the optimization of homogeneous catalysts: Ullmann ether formation. J. Am. Chem. Soc. 2000, 122, 5043-5051.
21. Hassan, J.; Sevifnon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-aryl bond formation one century after the discovery of the ullmann reaction. Chem. Rev. 2002, 102, 1359-1470.
22. Ley, S.V.; Thomas, A.W. Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation. Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
23. 2O nanocubes and subsequent oxidation to CuO hollow nanostructures for lithium-ion battery anode materials. Adv. Mater. 2009, 21, 803-807.
24. Kim, J.Y.; Park, J.C.; Kang, H.; Song, H.; Park, K.H. CuO Hollow Nanostructures catalyzed [3+2] cycloaddition of azides with terminal alkynes. Chem. Commun. 2010, doi:1039/b917781g.
25. Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Highly efficient copper-catalyzed N-arylation of alkylamines with aryl iodides using phosphoramidite as ligand. Catalysis Commun. 2005, 6, 784-787.
26. Guo, X.; Rao, H.; Fu, H.; Jiang, Y.; Zhaoa, Y. An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles. Adv. Synth. Catal. 2006, 348, 2197-2202.
27. Liu, Y.; Bai, Y.; Zhang, J.; Li, Y.; Jiao, J.; Qi, X. Optimization of the conditions for Copper-Mediated N-Arylation of Heteroarylamines. Eur. J. Org. Chem. 2007, 6084-6088.
28. Zhu, L.; Guo, P.; Li, G.; Lan, J.; Xie, R.; You, J. Simple copper Salt-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides. J. Org. Chem. 2007, 72, 8535-8538