Palladium-catalyzed cyanation reaction of aryl halides using K 4[Fe(CN)6] as non-toxic source of cyanide undermicrowave irradiation

Applied Organometallic Chemistry

Volumn 24, Issue 6, 2010, Pages 454-457

  Hajipour, Abdol R ^a,b   Karami, Kazem ^b   Pirisedigh, Azadeh ^b  

^a UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^b ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Catalyst; Cyanation reaction; K4 Fe(CN)6

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYL HALIDES; ARYL IODIDES; ARYL NITRILE; CATALYTIC AMOUNTS; CYANATION REACTION; EFFICIENT CATALYSTS; EFFICIENT METHOD; PALLADIUM COMPLEXES; PALLADIUM-CATALYZED CYANATION; SHORT REACTION TIME;

BROMINE COMPOUNDS; CATALYSTS; CHLORINE COMPOUNDS; CYANIDES; IRRADIATION; METAL HALIDES; MICROWAVE IRRADIATION; PALLADIUM; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

EID: 77952521766     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1639     Document Type: Article

References (49)

1. S. A. Weissman,D. Zewge, C. Chen, J. Org. Chem. 2005, 70, 1508.
2. T. Schareina, A. Zapf, M. Beller, Tetrahedron Lett. 2005, 46, 2585.
3. A. Zhang, J. L. Neumeyer, Org. Lett. 2003, 5, 201.
4. O. Grossman, D. Gelman, Org. Lett. 2006, 8, 1189.
5. M. R. Pitts, P.McCormack, J. Whittall, Tetrahedron 2006, 62, 4705.
6. T. Schareina,A. Zapf, M. Beller, J.Organomet.Chem. 2004, 689, 4576.
7. R. C. Larock, Comprehensive Organic Transformations, VCH: New York, 1989, 819;
8. C. Grundmann, in Houben-Weyl: Methoden der organischen Chemie, 4th ed. (Ed.: J. Falbe), Georg Thieme: Stuttgart, 1985, 5, 1313.
9. M. Chihiro, H. Nagamoto, I. Takemura, K. Kitano, H. Komatsu, K. Sekiguchi, F. Tabusa, T. Mori, M. Tominaga, Y. Yabuuchi, J. Med. Chem. 1995, 38, 353;
10. I. K. Khanna, R. M.Weier, Y. Yu, X. D. Xu, F. J. Koszyk, P. W. Collins, C. M. Koboldt, A. W. Veenhuizen, W. E. Perkins, J. J. Casler, J. L. Masferrer, Y. Y. Zhang, S. A. Gregory, K. Seibert, P. C. Isakson, J.Med. Chem. 1997, 40, 1634.
11. C. Yang, J. M. Williams, Org. Lett. 2004, 6, 2837.
12. S. J. Wittenberger, Org. Prep. Proc. Int. 1994, 26, 499;
13. J. C. Hodes, J. M. Hamby, C. J. Blankley, Drugs Future 1992, 17, 575;
14. H. Singh, A. S. C. Chawala, V. K. Kapoor, D. Paul, R. K. Malhotra, Prog. Med. Chem. 1980, 17, 151.
15. D. F. Mowry, Chem. Rev. 1948, 42, 189;
16. K. W. Rosenmund, E. Struck, Chem. Ber. 1919, 52, 1749.
17. Z. Qiong, H. Chi, X. Guangyong, X. Chongwen, C. Yuanyin, Synth. Commun. 1999, 29, 2349.
18. N. Suzuki, Y. Kaneko, T. Nomoto, Y. Izawa, J. Chem. Soc., Chem. Commun. 1984, 22, 1523.
19. I. P. Beletskaya, A. S. Sigeev, A. S. Peregudov, P. V. Petrovskii, J. Organomet. Chem. 2004, 689, 3810.
20. T. Schareina, A. Zapf,M. Beller, J.Organomet.Chem. 2004, 689, 4576.
21. R. R. Srivastava, S. E. Collibee, Tetrahedron Lett. 2004, 45, 8895.
22. Y. Ren, Z. Liu, S. Zhao, X. Tian, J. Wang,W. Yin, S. He, Catal. Commun. 2009, 10, 768.
23. J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890.
24. B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. J. Wepsiec, Org. Chem. 1998, 63, 8224.
25. M. Sundermeier, S. Mutyala, A. Zapf, A. Spannenberg, M. Beller, J. Organomet. Chem. 2003, 684, 50.
26. N. Chatani, T. Hanafusa, J. Org. Chem. 1986, 51, 4714.
27. H. E. Zieger, S. Wo, J. Org. Chem. 1994, 59, 3838.
28. H. R. Chobanian,B. P. Fors,L. S. Lin, TetrahedronLett. 2006, 47, 3303.
29. R. S. Jensen, A. S. Gajare, K. Toyota, M. Yoshifujia, F. Ozawab, Tetrahedron Lett. 2005, 46, 8645.
30. M. Hatsuda, M. Seki, Tetrahedron 2005, 61, 9908.
31. A. Littke, M. Soumeillant, R.F. Kaltenbach, R. J. Cherney, C. M. Tarby, S. Kiau, Org. Lett. 2007, 9, 1711.
32. K. M. Marcantonio, L. F. Frey, Y. Liu, Y. Chen, J. Strine, B. Phenix, D. J.Wallace, C. Y. Chen, Org. Lett. 2004, 6, 3723.
33. T. Schareina, A. Zapf, M. Beller, Chem. Commun. 2004, 1388.
34. S. Velmathi,N. E. Leadbeater, Tetrahedron Lett. 2008, 49, 4693.
35. T. Schareina, A. Zapf,W. Mägerlein, N. Müller, M. Beller, Tetrahedron Lett. 2007, 48, 1087.
36. N. S. Nandurkar, B. M. Bhanage, Tetrahedron 2008, 64, 3655.
37. Y. Sakakibara, Y. Ido, K. Sasaki,M. Sakai,N. Uchino, Bull.Chem. Soc. Jpn.1993, 66, 2776;
38. L. Cassar,M. Foa, F. Montanarai,G.P. Marinelli. J. Organomet. Chem. 1979, 173, 335.
39. C. Yang, J. M.Williams, Org. Lett. 2004, 6, 2837;
40. B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. JWepsiec, Org. Chem. 1998, 63, 8224.
41. N. E. Leadbeater, Chem. Commun. 2005, 2881;
42. P. Appukkuttan, E. Van der Eycken, W. Dehaen, Synlett 2003, 1204;
43. M. Erdelyi, A. Gogoll, J. Org. Chem. 2001, 66, 4165.
44. M. Alterman, A. Hallberg, J. Org. Chem. 2000, 65, 7984.
45. A. R. Hajipour, K. Karami, A. Pirisedigh, A. E. Ruoho, J. Organomet. Chem. 2009, 694, 2548.
46. S. E. Mallakpoor,A. R. Hajipour, K. Faghihi, Poly. Inter. 2000, 49, 1383.
47. A. R. Hajipour,S. E. Mallakpoor,H. Backnejad, Synth.Commun.2000, 30, 3855.
48. S. E. Mallakpoor, A. R. Hajipour, S. Khoee, Appl. Poly. Sci. 2000, 77, 3003.
49. A. R. Hajipour, B. Kooshki, A. E. Ruoho, Tetrahedron Lett. 2005, 46, 5503.