A state-of-the-art cyanation of aryl bromides: A novel and versatile copper catalyst system inspired by nature

Chemistry - A European Journal

Volumn 13, Issue 21, 2007, Pages 6249-6254

  Schareina, Thomas ^a   Zapf, Alexander ^a   Mägerlein, Wolfgang ^b   Müller, Nikolaus ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b Saltigo GmbH   (Germany)

Author keywords

Alkylimidazoles; Bromoarenes; Copper; Cyanation; Nitriles

Indexed keywords

CATALYST ACTIVITY; CYANIDES; HALOGEN COMPOUNDS; LIGANDS; STEREOSELECTIVITY;

ALKYLIMIDAZOLES; BROMOARENES; COPPER CATALYST SYSTEMS; CYANATION;

COMPLEXATION;

BROMIDE; BROMOBENZENE; COPPER; CYANIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BROMIDES; BROMOBENZENES; CATALYSIS; COPPER; CYANIDES; MOLECULAR STRUCTURE;

EID: 34547161471     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700079     Document Type: Article

References (48)

1. a) R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, 819;
2. b) C. Grundmann, in Houben-Weyl: Methoden der organischen Chemie, Vol. E5 (Ed.: J. Falbe), 4th ed., Georg Thieme, Stuttgart, 1985, 1313.
3. J. Lindley, Tetrahedron 1984, 40, 1433.
4. For a recent catalytic variant of the Sandmeyer reaction see: I. P. Beletskaya, A. S. Sigeev, A. S. Peregudov, P. V. Petrovskii, J. Organomet. Chem. 2004, 689, 3810.
5. For recent examples see: a) A. Martin, N. V. Kalevaru, B. Lücke, J. Sans, Green Chem. 2002, 4, 481;
6. b) Y. Liu, M. Zhong, W. Yu, Y. L. Ma, Synth. Commun. 2005, 35, 2951;
7. c) E. Rombi, I. Ferino, R. Monaci, C Picciau, V. Solinas, R. Buzzoni, Appl. Catal. A 2004, 266, 73;
8. d) B. Lücke, K. V. Narayana, A. Martin, K. Jähnisch, Adv. Synth. Catal. 2004, 346, 1407.
9. a) F. Hagedorn, H.-P. Gelbke in Ullmanns Encyklopädie der technischen Chemie, Vol. 17 (Eds. E. Bartholomé, E. Biekert, H. Hellmann, H. Ley, W. M. Weigert, E. Weise), 4th ed., Verlag Chemie, einheim, 1979, 333;
10. b) G. P. Ellis, T. M. Romney-Alexander, Chem. Rev. 1987, 87, 779.
11. K. Takagi, T. Okamoto, Y. Sakakibara, S. Oka, Chem. Lett. 1973, 471.
12. D. M. Tschaen, R. Desmond, A. O. King, M. C Fortin, B. Pipik, S. King, T. R. Verhoeven, Synth. Commun. 1994, 24, 887.
13. M. Sundermeier, A. Zapf, M. Beller, Eur. J. Inorg. Chem. 2003, 3513.
14. M. Sundermeier, A. Zapf, M. Beller, J. Sans, Tetrahedron Lett. 2001, 42, 6707.
15. J. Ramnauth, N. Bhardwaj, P. Renton, S. Rakhit, S. P. Maddaford, Synlett 2003, 2237.
16. M. Sundermeier, A. Zapf, M. Beller, Angew. Chem. 2003, 115, 1700;
17. Angew. Chem. Int. Ed. 2003, 42, 1661.
18. M. Sundermeier, S. Mutyala, A. Zapf, A. Spannenberg, M. Beller, J. Organomet. Chem. 2003, 684, 50.
19. H. R. Chobanian, B. P. Fors, L. S. Lin, Tetrahedron Lett. 2006, 47, 3303.
20. Recent examples: a) R. S. Jensen, A. S. Gajare, K. Toyota, M. Yoshifuji, F. Ozawa, Tetrahedron Lett. 2005, 46, 8645;
21. b) J. M. Veauthier, C. N. Carlson, G. E. Collis, J. L. Kiplinger, K. D. John, Synthesis 2005, 2683;
22. c) R. Chidambaram, Tetrahedron Lett. 2004, 45, 1441.
23. 6] and € 6.6 for KCN; source Aldrich Chemicals Catalogue 2006.
24. a) T. Schareina, A. Zapf, M. Beller, Chem. Commun. 2004, 1388;
25. b) T. Schareina, A. Zapf, M. Beller, J. Organomet. Chem. 2004, 689, 4576;
26. c) T. Schareina, A. Zapf, W. Mägerlein, N. Müller, M. Beller, Tetrahedron Lett. 2007, 48, 1087.
27. T. Schareina, A. Zapf, M. Beller, Tetrahedron Lett. 2005, 46, 2585.
28. a) S. A. Weissman, D. Zewge, C. Chen, J. Org. Chem. 2005, 70, 1508;
29. b) O. Grossmann, D. Gelman, Org. Lett. 2006, 8, 1189.
30. T. Schareina, A. Zapf, W. Mägerlein, N. Müller, M. Beller, Synlett 2007, 555.
31. J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890.
32. H.-J. Cristau, A. Ouali, J.-F. Spindler, M. Taillefer, Chem. Eur. J. 2005, 11, 2483.
33. a) V. Sendra, D. Cannella, B. Bersch, F. Fieschi, S. Menage, D. Lascoux, J. Coves, Biochemistry 2006, 45, 5557;
34. b) D. Hernandez-Romero, A. Sanchez-Amat, F. Solano, FEBS Lett. 2006, 273, 257;
35. c) T. Klabunde, C. Eicken, J. C. Sacchettini, B. Krebs, Nat. Struct. Biol. 1998, 5, 1084;
36. d) K. Brown, M. Tegoni, M. Prudencio, A. S. Pereira, S. Besson, J. J. Moura, I. Moura, C Cambillau, Nat. Struct. Biol. 2000, 7, 191.
37. a) E. Fadda, N. Chakrabarti, R. Pomes, J. Phys. Chem. B 2005, 109, 22629;
38. b) C. D. Syme, R. C Nadal, S. E. J. Rigby, J. H. Viles, J. Biol. Chem. 2004, 279, 18169;
39. c) C.S. Atwood, G. Perry, H. Zeng, Y. Kato, W. D. Jones, K. Q. Ling, X. D. Huang, R. D. Moir, D. D. Wang, L. M. Sayre, M. A. Smith, S. G. Chen, A. I. Bush, Biochemistry 2004, 43, 560;
40. d) M. Nakamura, T. Nakajima, Y. Ohba, S. Yamauchi, B. R. Lee, E. Ichishima, Biochem. J. 2000, 350, 537;
41. e) L. Banci, I. Bertini, S. Ciofi-Baffoni, E. Katsari, N. Katsaros, K. Kubicek, S. Mangani, Proc. Natl. Acad. Sci. USA 2005, 102, 3994.
42. For the application of 1-alkylimidazoles as solubilizing additives see: a) J. A. Welleman, F. B. Hulsbergen, J. Reedijk, Makromol. Chem. 1981, 182, 785;
43. b) J. Zhou, G. C Fu, J. Am. Chem. Soc. 2003, 125, 12527.
44. Initial amination reactions of bromobenzenes in the presence of Cu/1-butylimidazole showed that these catalysts are also active for other coupling reactions.
45. J. Stetter, F. Lieb, Angew. Chem. 2000, 112, 1792;
46. Angew. Chem. Int. Ed. 2000, 39, 1124.
47. a) K. Isobe, S. Kawaguchi, Heterocycles 1981, 16, 1603;
48. b) M. Beller, W. Mägerlein, A. F. Indolese, C Fischer, Synthesis 2001, 1098.