Tetrazole-1-acetic acid as a ligand for copper-catalyzed N-arylation of imidazoles with aryl iodides under mild conditions

Chinese Chemical Letters

Volumn 24, Issue 10, 2013, Pages 893-896

  Wu, Feng Tian ^a   Liu, Ping ^a   Ma, Xiao Wei ^a   Xie, Jian Wei ^a   Dai, Bin ^a  

^a SHIHEZI UNIVERSITY   (China)

Author keywords

Aryl iodides; Copper; N Arylation Imidazoles; Tetrazole 1 acetic acid

Indexed keywords

EID: 84883739637     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.05.037     Document Type: Article

References (21)

1. For some selected reviews, see: H. Gao, and J.M. Shreeve Azole-based energetic salts Chem. Rev. 111 2011 7377 7436
2. Z. Jin Muscarine, imidazole, oxazole and thiazole alkaloids Nat. Prod. Rep. 22 2005 196 229
3. O. Kühl The chemistry of functionalized N-heterocyclic carbenes Chem. Soc. Rev. 36 2007 592 607
4. J. Lindley Tetrahedron report number 163: copper assisted nucleophilic substitution of aryl halogen Tetrahedron 40 1984 1433 1456
5. A. Kiyomori, J.F. Marcoux, and S.L. Buchwald An efficient copper-catalyzed coupling of aryl halides with imidzoles Tetrahedron Lett. 40 1999 2657 2660
6. 1-benzyl substituted imidazole-4-and imidazole-5-carbaldhydes Synthesis 1983 1983 47 49
7. A. Klapars, J.C. Antilla, X. Huang, and S.L. Buchwald A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles J. Am. Chem. Soc. 123 2001 7727 7729
8. M. Taillefer, H.J. Cristau, P. Cellier, J.F. Spindler, Relatively Low-Temperature Catalytic Procedure For Arylation or Vinylation of Nitrogen-Containing Nucleophilic Compounds, Fr 2833947-WO 0353225 (Priority Number Fr 16547, 2001).
9. For some selected reviews, see: Z. Li, Z. Wu, H. Deng, and X. Zhou Progress in copper-catalyzed Ullmann-type coupling reactions in water Chin. J. Org. Chem. 33 2013 760 770 (in Chinese)
10. F. Monnier, and M. Taillefer Catalytic CC, CN, and CO Ullmann-type coupling reactions Angew. Chem. Int. Ed. 48 2009 6954 6971
11. J.D. Senra, L.C.S. Aguiar, and A.B.C. Simas Recent progress in transition-metal-catalyzed CN cross-couplings: emerging approaches towards sustainability Curr. Org. Synth. 8 2011 53 78
12. F. Monnier, and M. Taillefer Catalytic CC, CN, and CO Ullmann-type coupling reactions: copper makes a difference Angew. Chem. Int. Ed. 47 2008 3096 3099
13. Y. Wang, J. Zeng, and X. Cui Recent progress in copper-catalyzed CN coupling reactions Chin. J. Org. Chem. 30 2010 181 199
14. 4 cluster arrays Inorg. Chem. 43 2004 6133 6135
15. X.Q. Zhang, Q. Yu, H.D. Bian, X.G. Bao, and H. Liang Synthesis, structures, and characterization of cadmium(II), cobalt(II), and copper(II) metal polymers with tetrazole-1-acetate J. Coord. Chem. 62 2009 2108 2117
16. 2O) (tza = tetrazole-1-acetic acid) Chin. J. Struct. Chem. 30 2011 431 437
17. Q. Yu, X. Zhang, and H. Bian pH-dependent Cu(II) coordination polymers with tetrazole-1-acetic acid: synthesis, crystal structures, EPR and magnetic properties Cryst. Growth Des. 8 2008 1140 1146
18. n Chem. J. Chin. Univ. 32 2011 1870 1875 (in Chinese)
19. Y. Jiao, N. Yan, and J. Xie A simple and efficient copper(II) complex as a catalyst for N-arylation of imidazoles Chin. J. Chem. 31 2013 267 270
20. J. Xie, X. Zhu, and M. Huang Pyrrole-2-carbohydrazides as ligands for Cu-catalyzed amination of aryl halides with amines in pure water Eur. J. Org. Chem. 2010 3219 3223
21. 3/PEG-water: an efficient catalytic system for cross coupling reaction of aryl iodides and alkynes Synth. Commun. 41 2011 3123 3133