Synthesis, spectral characterization, electrochemical studies and catalytic properties in Suzuki-Miyaura coupling reactions of the mononuclear Pd II, trinuclear PdII(BPh2)2 and RuII-PdII-RuII type complexes containing 4-amino-1-benzyl piperidine and phenyl groups

Applied Organometallic Chemistry

Volumn 22, Issue 9, 2008, Pages 494-502

  Kilic, Ahmet ^a   Yilmaz, Ismail ^b   Ulusoy, Mahmut ^c   Tas, Esref ^a  

^a HARRAN UNIVERSITY   (Turkey)

^b ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

^c EGE UNIVERSITY   (Turkey)

Author keywords

Catalytic activity; Cross coupling; Electrochemistry; Ru(II) metal complexes; Spectroscopy; Suzuki Miyaura reactions; Synthesis

Indexed keywords

AMINATION; SPECTRUM ANALYZERS;

CATALYTIC ACTIVITY; CROSS-COUPLING; ELECTROCHEMISTRY; RU(II) METAL COMPLEXES; SPECTROSCOPY; SUZUKI-MIYAURA REACTIONS; SYNTHESIS;

ELECTROCHEMICAL PROPERTIES;

EID: 51349119716     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1430     Document Type: Article

References (67)

1. M. Kurtoglu, M. M. Dagdelen, S. Toroglu, Trans.Met. Chem. 2006, 31, 382;
2. b) R. B. Lauffer, Chem. Rev. 1987, 87, 190;
3. c) G. T. Muise, X. Li, D. R. Powell, Inorg. Chim. Acta 2004, 357, 1134.
4. A. Chakravorty, Coord. Chem. Rev. 1974, 13, 1.
5. J. P. Leonardo, D. P. Novotnik, R. D. Neirinckx, J. Nucl. Med. 1986, 27, 1819.
6. J. R. Dilwort, S. J. Parrott, Chem. Soc. Rev. 1998, 27, 43.
7. I. H. Hall, K. F. Bastow, A. E. Warren, C. R. Barnes, G. M. Bouet, Appl. Organometal. Chem. 1999, 13, 819.
8. E. Lukevics, R. Abele, M. Fleisher, J. Popelis, E. Abale, J. Mol. Catal. A Chem. 2003, 198, 89.
9. D. Sellman, J. Utz, F. W. Heinemann, Inorg. Chem. 1999, 38, 459.
10. M. C. M. Laranleira, R. A. Marusak, A. G. Lappin, Inorg. Chim. Acta 2000, 186, 300.
11. K. Ohta, R. Hisaghi, M. I. Kejima, I. Yamamoto, N. Kobayashi, J. Mater. Chem. 1998, 8, 1979.
12. S. Kumar, R. Singh, H. Singh, J. Chem. Soc. Perkin Trans. 1992, 1, 3049.
13. N. Miyaruna, A. Suzuki, Chem. Rev. 1995, 95, 2457;
14. b) A. J. Suzuki, J. Organomet. Chem. 1999, 576, 147;
15. c) S. P. Stanforth, Tetrahedron 1998, 54, 263;
16. d) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427;
17. e) N. J. Whitcombe, K. K. Hii, S. E. Gibson, Tetrahedron 2001, 57, 7449;
18. f) N. T. S. Phan, M. V. D. Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609;
19. g) F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2008, 64, 3047.
20. S. Haber, H. J. Kleiner, (Hoescht AG), DE 19527118 [Chem. Abstr. 1997, 126, 185894];
21. b) L. Botella, C. Najera, Angew. Chem. Int. Edn 2002, 41, 179.
22. M. L. Kantouri, C. D. Papadopolous, M. Quiros, A. G. Hatzidimitriou, Polyhedron 2006, 26, 1292;
23. b) S. Srinirasam, J. Annaraj, P. R. Athappan, J. Inorg. Biochem. 2005, 99, 876.
24. F. Karapcin, S. Ilican, Y. Caglar, M. Caglar, B. Dede, Y. Sahin, J. Organomet. Chem. 2007, 692, 2473.
25. B. P. Sullivan, J. A. Baumann, T. J. Meyer, D. J. Salmon, H. Lehmann, A. Ludi, J. Am. Chem. Soc. 1977, 99, 7368;
26. b) W. H. Fung, W. Y. Fu, C. M. Che, J. Org. Chem. 1998, 63, 7715;
27. c) T. H. Ghaddar, E. W. Castner, S. S. Isied, J. Am. Chem. Soc. 2000, 122, 1233.
28. B. J. Sullivan, D. J. Salmon, T. J. Meyer, Inorg. Chem. 1978, 17, 3334.
29. R. Llanguri, J. J. Morris, W. C. Stanley, E. T. Bell-Loncella, M. Turner, W. J. Bayko, C. A. Bessel, Inorg. Chim. Acta 2001, 315, 53.
30. A. Kilic, E. Tas, I. Yilmaz, J. Chem. Sci. (in press).
31. B. R. Manzano, F. A. Jalon, G. Espino, A. Guerrero, R. M. Claramunt, C. Escolastico, J. Elguero, M. A. Heras, Polyhedron 2007, 26(15), 4373;
32. b) P. J. Steel, E. C. Constable, J. Chem. Soc. Dalton Trans. 1990, 1389.
33. M. Durmus, V. Ahsen, D. Luneau, J. Pecaut, Inorg. Chim. Acta 2004, 357, 588.
34. 13C-NMR- Spektroskopie. Georg Thieme: New York, 1984.
35. Y. Gok, H. Kantekin, H. Alp, M. Ozdemir, Z. Anorg. Allg. Chem. 1995, 621, 1237.
36. E. Bell-Loncella, C. A. Bessel, Inorg. Chim. Acta 2000, 303, 199;
37. b) F. E. Lytle, L. M. Petrosky, L. R. Carlson, Anal. Chim. Acta 1971, 57, 239.
38. K. N. Kumar, R. Ramesh, Polyhedron 2005, 24, 1885;
39. b) A. Kilic, E. Tas, B. Gumgum, I. Yilmaz, Trans. Met. Chem. 2006, 31, 645.
40. S. A. Ali, A. A. Soliman, M. M. Aboaly, R. M. Ramadan, J. Coord. Chem. 2002, 55, 1161.
41. M. Kandaz, A. Koca, A. R. Ozkaya, Polyhedron 2004, 23, 1987;
42. b) E. Tas, M. Aslanoglu, A. Kilic, Z. Kara, J. Coord. Chem. 2006, 59(8), 861.
43. M. R. Rosenthall, T. Chem. Edu. 1973, 50, 331.
44. F. Karapcin, B. Dede, Y. Caglar, D. Hur, S. Ilican, M. Caglar, Y. Sahin, Optics Comm. 2007, 272, 131.
45. L. Sacconi, M. Ciampolini, F. Maffio, F. P. Cavasino, J. Am. Chem. Soc. 1962, 84, 3245;
46. b) A. Kilic, E. Tas, B. Deveci, I. Yilmaz, Polyhedron 2007, 26, 4009.
47. R. L. Carlin, Transition Metal Chemistry, vol. 1. Marcel Dekker: New York, 1965.
48. C. Fraser, B. Bosnich, Inorg. Chem. 1994, 33, 338;
49. b) S. Ilhan, H. Temel, I. Yilmaz, A. Kilic, Trans. Met. Chem. 2007, 32, 344.
50. A. B. P. Lever, Inorganic Electronic Spectroscopy. Elsevier: Amsterdam, 1984;
51. b) E. Tas, V. T. Kasumov, O. Sahin M. Ozdemir, Trans. Met. Chem. 2002, 27, 442.
52. R. Hage, J. H. Van Diemen, G. Ehrlich, J. G. Haasnoot, D. J. Stufkens, T. L. Snoeck, J. G. Vos, J. Reedjick, Inorg. Chem. 1990, 29, 988;
53. b) M. Murali, M. Palaniandavar, Polyhedron 2007, 26(14), 3980.
54. R. L. Dutta, Inorganic Chemistry, Part II, 2nd edn. The New Book Stall: Calcutta, 1981, p. 386;
55. b) A. Kilic, E. Tas, B. Gumgum, and I. Yilmaz, Polish J. Chem. 2006, 80, 1967;
56. c) M. S. Refat, S. A. El-Korashy, D. N. Kumar, A. S. Ahmad, Spectrochim. Acta A (doi:10.1016/j.saa.2007.10.005);
57. d) M. S. Refat, J. Mol. Struct. 2007, 742(1-3), 24.
58. B. R. Srinivasan, N. S. Dhuri, C. Nathar, and W. Bensch, Trans. Met. Chem. 2007, 32, 64;
59. b) A. Kilic, and E. Tas, Synth. React. Inorg. Met.-Org. Chem. and Nano-Met. Chem. 2007, 37, 583.
60. X. Liu, J. Liu, K. Jin, X. Yang, Q. Peng, L. Sun, Tetrahedron 2005, 61, 5655.
61. B. Gumgum, N. Biricik, F. Durap, I. Ozdemir, N. Gurbuz, W. H. Ang, P. J. Dyson, Appl. Organometal. Chem. 2007, 21, 711.
62. A. F. Littke, G. F. Fu, Angew. Chem. Int. Edn Eng. 2002, 41, 4176;
63. b) R. B. Bedford, S. L. Hazewood, M. E. Limmeat, Chem. Commun. 2002, 2610.
64. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
65. N. J. Whitcombe, K. K. Hii (Mimi), S. E. Gibson, Tetrahedron 2001, 57, 7449;
66. b) M. Keles, Z. Aydin, O. Serindag, J. Organomet. Chem. 2007, 692, 1951.
67. C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804.