New palladium complexes with S- or Se-containing schiff-base ligands as efficient catalysts for the Suzuki-Miyaura cross-coupling reaction of aryl bromides with phenylboronic acid under aerobic conditions

European Journal of Inorganic Chemistry

Volumn , Issue 13, 2006, Pages 2642-2646

  Kostas, Ioannis D ^a   Steele, Barry R ^a   Terzis, Aris ^b   Amosova, Svetlana V ^c   Martynov, Alexander V ^c   Makhaeva, Natalia A ^c  

^a INSTITUTE OF BIOLOGY   (Greece)

^b INSTITUTE OF MATERIALS SCIENCE   (Greece)

^c A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

C C coupling; Homogeneous catalysis; Schiff bases; Suzuki; Tridentate ligands

Indexed keywords

CATALYSIS; CHELATION; METAL HALIDES; ORGANIC ACIDS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ARYL BROMIDES; C-C COUPLING; HOMOGENEOUS CATALYSIS; PALLADIUM COMPLEXES; PHENYLBORONIC ACIDS; SALICYLALDEHYDE; SCHIFF-BASE; SCHIFF-BASE LIGANDS; SUZUKI; TRIDENTATE LIGANDS;

LIGANDS;

EID: 33745880393     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600180     Document Type: Article

References (55)

1. Recent selected books: a) J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995;
2. b) F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998;
3. c) M. T. Reetz, Transition Metal Catalysed Reactions (Eds.: S. G. Davies, S.-I. Murahashi), Blackwell Science, Oxford, 1999;
4. d) N. Miyaura, Cross-Coupling Reactions, Springer, Berlin, 2002.
5. Recent selected reviews: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
6. b) S. P. Stanforth, Tetrahedron 1998, 54, 263-303;
7. c) A. Suzuki, J. Organomet. Chem. 2002, 655, 83-90;
8. d) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59;
9. e) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176-4211;
10. f) A. Zapf, M. Beller, Top. Catal. 2002, 19, 101-109;
11. g) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283-2321;
12. h) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419-2440;
13. i) A. C. Frisch, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 674-688.
14. G. Bringmann, C. Gunther, M. Ochse, O. Schupp, S. Tasler in Progress in the Chemistry of Organic Natural Products (Eds.: W. Hertz, H. Falk, G. W. Kirby, R. Moore), Springer, New York, 2001, vol. 82, pp. 1-293.
15. Recent selected papers: a) R. B. Bedford, C. S. J. Cazin, M. B. Hursthouse, M. E. Light, V. J. M. Scordia, Dalton Trans. 2004, 3864-3868;
16. b) M. an der Heiden, H. Plenio, Chem. Eur. J. 2004, 10, 1789-1797;
17. c) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 38-39;
18. d) K. W. Anderson, S. L. Buchwald, Angew. Chem. Int. Ed. 2005, 44, 6173-6177;
19. e) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696;
20. f) W-M. Dai, Y. Zhang, Tetrahedron Lett. 2005, 46, 1377-1381;
21. g) D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett. 2005, 7, 4907-4910;
22. h) M. Dochnahl, M. Doux, E. Faillard, L. Ricard, P. Le Floch, Eur. J. Inorg. Chem. 2005, 125-134;
23. i) C. Bianchini, G. Lenoble, W. Oberhauser, S. Parisel, F. Zanobini, Eur. J. Inorg. Chem. 2005, 4794-4800;
24. j) R. C. Smith, C. R. Bodner, M. J. Earl, N. C. Sears, N. E. Hill, L. M. Bishop, N. Sizemore, D. T. Hehemann, J. J. Bohn, J. D. Protasiewicz, J. Organomet. Chem. 2005, 690, 477-481;
25. k) J. Gong, G. Liu, C. Du, Y. Zhu, Y. Wu, J. Organomet. Chem. 2005, 690, 3963-3969.
26. Recent selected papers: a) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1363-1365;
27. b) J. S. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341;
28. c) I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, G. Sánchez, G. López, J. L. Serrano, L. García, J. Pérez, E. Pérez, Dalton Trans. 2004, 3970-3981;
29. d) I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, Org. Lett. 2004, 6, 4435-4438;
30. e) R. A. Gossage, H. A. Jenkins, P. N. Yadav, Tetrahedron Lett. 2004, 45, 7689-7691;
31. f) A. Mukherjee, A. Sarkar, Tetrahedron Lett. 2005, 46, 15-18;
32. g) A. I. Moncada, M. A. Khan, L. M. Slaughter, Tetrahedron Lett. 2005, 46, 1399-1403;
33. h) C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron 2005, 61, 7438-7446;
34. i) T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem. 2005, 70, 2191-2194;
35. j) C-L. Chen, Y.-H. Liu, S.-M. Peng, S.-T. Liu, Organometallics 2005, 24, 1075-1081.
36. Recent selected papers: a) I. D. Kostas, J. Organomet. Chem. 2001, 626, 221-226;
37. b) I. D. Kostas, J. Organomet. Chem. 2001, 634, 90-98;
38. c) I. D. Kostas, Inorg. Chim. Acta 2003, 355, 424-427;
39. d) I. D. Kostas, B. R. Steele, A. Terzis, S. V. Amosova, Tetrahedron 2003, 59, 3467-3473;
40. e) I. D. Kostas, B. R. Steele, F. J. Andreadaki, V. A. Potapov, Inorg. Chim. Acta 2004, 357, 2850-2854;
41. f) I. D. Kostas, K. A. Vallianatou, J. Holz, A. Börner, Appl. Organomet. Chem. 2005, 19, 1090-1095.
42. a) D. Kovala-Demertzi, P. N. Yadav, M. A. Demertzis, J. P. Jasinski, F. J. Andreadaki, I. D. Kostas, Tetrahedron Lett. 2004, 45, 2923-2926;
43. b) I. D. Kostas, F. J. Andreadaki, D. Kovala-Demertzi, C. Prentjas, M. A. Demertzis, Tetrahedron Lett. 2005, 46, 1967-1970.
44. S. V. Amosova, N. A. Makhaeva, A. V. Martynov, V. A. Potapov, B. R. Steele, I. D. Kostas, Synthesis 2005, 1641-1648.
45. A. D. Garnovskii, I. S. Vasil'chenko, Usp. Khim. 2002, 71, 1064-1089.
46. G. C. Percy, D. A. Thornton, J. Inorg. Nucl. Chem. 1972, 34, 3369-3376.
47. M. T. Reetz, J. G. De Vries, Chem. Commun. 2004, 1559-1563.
48. a) R. X. Wang, X. Z. You, Q. J. Merg, E. A. Minz, X. R. Bu, Synth. Commun. 1994, 24, 1757-1760;
49. b) S. Matsui, M. Mitani, J. Saito, Y. Tohi, H. Makio, N. Matsukawa, Y. Takagi, K. Tsuru, M. Nitabaru, T. Nakano, H. Tanaka, N. Kashiwa, T. Fujita, J. Am. Chem. Soc. 2001, 123, 6847-6856.
50. J. Okuda, T. Eberle, T. P. Spaniol, V. Piquet-Fauré, J. Organomet. Chem. 1999, 591, 127-137.
51. 2b is a known compound but no NMR spectroscopic data were reported: S. Dhar, D. Senapati, P. K. Das, P. Chattopadhyay, M. Nethaji, A. R. Chakravarty, J. Am. Chem. Soc. 2003, 125, 12118-12124.
52. 2d was isolated as a viscous oil and used for complex formation without further purification. Analogous (butyl)Se- or (hexyl) Se-containing Schiff bases are known: a) H. Liang, J. Wu, Y. Liu, L. Yang, L. Hu, S. Qu, Biol. Trace Elem. Res. 2003, 92, 181-188;
53. b) C.-Y. Yang, Y. Liu, J. Wu, R. Li, Y.-J. Hu, S.-S. Qu, J. Pharm. Pharmacol. 2004, 56, 1127-1133.
54. G. M. Sheldrick, SHELXS-86, Structure Solving Program, University of Göttingen, Germany, 1986.
55. G. M. Sheldrick, SHELXL-97, Crystal Structure Refinement, University of Göttingen, Germany, 1997.