S-arylation of mercaptobenzimidazoles using Cu(I) catalysts - Experimental and theoretical observations

Tetrahedron Letters

Volumn 52, Issue 26, 2011, Pages 3347-3352

  Sekar, Ramkumar ^a   Srinivasan, Marutheeswaran ^b   Marcelis, Antonius T M ^c   Sambandam, Anandan ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b PONDICHERRY UNIVERSITY   (India)

^c WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Aryl iodide; C S cross coupling; Copper (I) catalyst; DFT calculation; MBI

Indexed keywords

1,10 PHENANTHROLINE; 2 BENZIMIDAZOLETHIOL DERIVATIVE; COPPER IODIDE; IODIDE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DENSITY FUNCTIONAL THEORY; VIBRATION;

EID: 79957688474     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.078     Document Type: Article

References (47)

1. R. Zou, K.R. Ayres, J.C. Drach, and L.B. Townsend J. Med. Chem. 39 1996 3477 3482
2. D. Carcanague, Y.K. Shue, M.A. Wuonola, M.U. Nickelsen, C. Joubran, J.K. Abedi, J.T. Jones, and C. Kühler J. Med. Chem. 45 2002 4300 4309
3. J.M. Shin, G. Sachs, Y.M. Cho, and M. Garst Molecules 14 2009 5247 5280
4. W. Huang, P.L. Zhao, C.L. Liu, Q. Chen, Z.M. Liu, and G.F. Yang J. Agric. Food Chem. 55 2007 3004 3010
5. N. Bennamane, K. Zaïoua, Y. Akacem, R. Kaoua, Y. Bentarzi, S. Bakhta, B.N. Kolli, and L. Uhab Org. Commun. 2 2009 49 59
6. J. Aljourani, K. Raeissi, and M.A. Golozar Corros. Sci. 51 2009 1836 1843
7. O.L. Humenyuk, O.I. Syza, and O.M. Krasovs'kyi Mater. Sci. 43 2007 91 101
8. H.P. Narkhede, U.B. More, D.S. Dalal, and P.P. Mahulikar J. Sci. Ind. Res. 67 2008 374 376
9. N.L. Dias Filho Mikrochim. Acta 130 1999 233 240
10. Cox, D.; Hall, D. E.; Ingall, A. H.; Suschitzky, J. L. Eur. Patent Appl. EP220053A2, CAN; 1987, 108, 94553.
11. A.R. Katritzky, and K. Akutagawa J. Org. Chem. 54 1989 2949 2952
12. E. Kotali, and A. Varvoglis J. Chem. Res., Synop. 1989 142
13. P. Lan, F.A. Romero, T.S. Malcolm, B.D. Stevens, D. Wodka, and G.M. Makara Tetrahedron Lett. 49 2008 1910 1914
14. S.M. Allin, W.R. Bowman, R. Karim, and S.S. Rahman Tetrahedron 62 2006 4306 4316
15. S.J. Teague, S. Barber, S. King, and L. Stein Tetrahedron Lett. 46 2005 4613 4616
16. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400 5449
17. W. Deng, Y. Zou, Y.F. Wang, L. Liu, and Q.X. Guo Synlett 2004 1254 1258
18. T. Kondo, and T. Mitsudo Chem. Rev. 100 2000 3205 3220
19. M.A. Fernandez-Rodriguez, Q. Shen, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 2180 2181
20. M.A. Fernandez-Rodriguez, and J.F. Hartwig J. Org. Chem. 74 2009 1663 1672
21. X. Ku, H. Huang, H. Jiang, and H. Liu J. Comb. Chem. 11 2009 338 340
22. T. Migita, T. Shimizu, Y. Asami, J.-I. Shiobara, Y. Kato, and M. Kosugi Bull. Chem. Soc. Jpn 53 1980 1385 1389
23. N. Zheng, J.C. McWilliams, F.J. Fleitz, J.D. Armstrong III, and R.P. Volante J. Org. Chem. 63 1998 9606 9607
24. Y. Zhang, K.N. Ngeow, and J.Y. Ying Org. Lett. 9 2007 3495 3498
25. V. Percec, J.Y. Bae, and D.H. Hill J. Org. Chem. 60 1995 6895 6903
26. K. Kunz, U. Scholz, and D. Ganzer Synlett 2003 2428 2439
27. E. Sperotto, G.P.M. van Klink, J.G. de Vries, and G. van Koten J. Org. Chem. 73 2008 5625 5628
28. C.G. Bates, R.K. Gujadhur, and D. Venkataraman Org. Lett. 4 2002 2803 2806
29. F.Y. Kwong, and S.L. Buchwald Org. Lett. 4 2002 3517 3520
30. S. Murru, H. Ghosh, S.K. Sahoo, and B.K. Patel Org. Lett. 11 2009 4254 4257
31. T. Doneux, F. Tielens, P. Geerlings, and C.B. Herman J. Phys. Chem. A. 110 2006 11346 11352
32. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Org. Lett. 11 2009 1697 1700
33. M. Alcolea Palafox, V.K. Rastogi, R.P. Tanwar, and L. Mittal Spectrochim. Acta, Part A 59 2003 2473 2486
34. 2OS: C, 40.19; H, 2.17; N, 6.70
35. A. Kiyomori, J.F. Marcoux, and S.L. Buchwald Tetrahedron Lett. 40 1999 2657 2660
36. C.S. Guy, and T.C. Jones Synlett 2009 2253 2256
37. J.M. Shin, Y.M. Cho, and G. Sachs J. Am. Chem. Soc. 126 2004 7800 7811
38. T. Cohen, J.W. La, and A.G. Dietz Tetrahedron Lett. 40 1974 3555 3558
39. J. Lindley Tetrahedron 40 1984 1433 1456
40. L. Rout, P. Saha, S. Jammi, and T. Punniyamurthy Eur. J. Org. Chem. 4 2008 640 643
41. R.G. Pearson J. Am. Chem. Soc. 85 1963 3533 3539
42. H. Bohlig, M. Ackermann, F. Billes, and M. Kudra Spectrochim. Acta, Part A 55 1999 2635 2646
43. gaussian 03. Frisch, M. J. et al. Gaussian, Inc., Pittsburgh, PA, 2003. (a) B3LYP is Becke's three parameter hybrid method with LYP correlation functional.
44. P.J. Stevens, F.J. Devlin, C.F. Chablowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623 11627
45. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B. 37 1988 785 789
46. S.H. Vosko, L. Wilk, and M. Nusair Can. J. Phys. 58 1980 1200 1211
47. L.M. Rodriguez-Valdez, W. Villamisar, M. Casales, J.G. Gonzalez-Rodriguez, A. Martinez-Villafine, L. Martinez, and D. Glossman-Mitnik Corros. Sci. 48 2006 4053 4064