Synthesis, structural elucidation and catalytic activity toward a model Mizoroki-Heck C-C coupling reaction of the pyrazolic Tröger's base Pd 4Cl8(PzTB)2 complex

Journal of Organometallic Chemistry

Volumn 696, Issue 9, 2011, Pages 1834-1839

  Cuenú, Fernando ^a,b   Abonia, Rodrigo ^b   Bolaños, Alberto ^b   Cabrera, Armando ^c  

^a UNIVERSIDAD DEL QUINDÍO   (Colombia)

^b UNIVERSIDAD DEL VALLE   (Colombia)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Metallomacrocycles; Mizoroki Heck reaction; Palladium(II) complexes; Pyrazole derivatives; Stilbenes; Tr ger's base

Indexed keywords

METALLOMACROCYCLES; MIZOROKI-HECK REACTION; PALLADIUM(II) COMPLEXES; PYRAZOLE DERIVATIVES; STILBENES;

ATOMIC SPECTROSCOPY; CATALYST ACTIVITY; STYRENE; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

EID: 79955017822     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.02.016     Document Type: Article

References (40)

1. J. Tröger J. Prakt. Chem. 63 1887 225 245
2. M.D. Cowart, I. Sucholeiki, R.R. Bukownik, and C.S. Wilcox J. Am. Chem. Soc. 110 1988 6204 6210
3. M. Demeunynck, and A. Tatibouët G.W. Gribble, T.L. Gilchrist, Prog. Heterocycl. Chem. 11 1999 Pergamon, Oxford 1 20
4. B.G. Bag Curr. Sci. 68 1995 279 288
5. S. Paliwal, S. Geib, and C.S. Wilcox J. Am. Chem. Soc. 116 1994 4497 4498
6. E. Kim, S. Paliwal, and C.S. Wilcox J. Am. Chem. Soc. 120 1998 11192 11193
7. K. Nakamura, and K.N. Houk Org. Lett. 1 1999 2049 2051
8. S. Goswami, and K. Ghosh Tetrahedron Lett. 38 1997 4503 4506
9. S. Goswami, K. Ghosh, and S. Dasgupta J. Org. Chem. 65 2000 1907 1914
10. A.P. Hansson, P.-O. Norrby, and K. Wärnmark Tetrahedron Lett. 39 1998 4565 4568
11. M. Miyake, and C.S. Wilcox Heterocycles 57 2002 515 522
12. A.A. Ibrahim, M. Matsumoto, Y. Miyahara, K. Izumi, M. Suenaga, N. Shimizu, and T. Inazu J. Heterocycl. Chem. 35 1998 209 215
13. B.G. Bag, and G. von Kiedrowski Angew. Chem. Int. Ed. 38 1999 3713 3714
14. Y. Goldberg, and H. Alper Tetrahedron Lett. 36 1995 369 372
15. M.S. Khoshbin, M.V. Ovchinnikov, C.A. Mirkin, J.A. Golen, and A.L. Rheingold Inorg. Chem. 45 2006 2603 2609
16. C. Bresson, M. Luhmer, M. Demeunynck, A. Kirsch-De Mesmaeker, and F. Pierard Tetrahedron Lett. 45 2004 2863 2866
17. O. Van Gijte, A. Tatibouët, M. Demeunynck, J. Lhomme, and A. Kirsch-De Mesmaeker Tetrahedron Lett. 38 1997 1567 1570
18. T. Weilandt, U. Kiehne, G. Schnakenburg, and A. Lützen Chem. Commun. 2009 2320 2322
19. R.F. Heck Pure Appl. Chem. 50 1978 691 701
20. R.F. Heck, and W.A. Herrmann Angew. Chem. Int. Ed. 41 2002 1290 1309
21. S. Bräse, and A. de Meijere A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions second ed. 2004 Wiley-VCH Weinheim, Germany 218 225
22. For the synthesis of compound 4 see
23. R. Abonia, A. Albornoz, H. Larrahondo, J. Quiroga, B. Insuasty, H. Insuasty, A. Hormaza, A. Sánchez, and M. Nogueras J. Chem. Soc. Perkin Trans. 1 2002 1588 1591
24. R. Abonia, E. Rengifo, J. Quiroga, B. Insuasty, A. Sánchez, J. Cobo, J.N. Low, and M. Nogueras Tetrahedron Lett. 43 2002 5617 5620
25. Compound 3 was obtained following a similar procedure as described by A.G.M. Mostafa-Hossain, T. Nagaoka, and K. Ogura Electrochim. Acta 41 1996 2773 2780
26. K. Nakamoto J. Wiley, Sons Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B sixth ed. 2009 Wiley-VCH Weinheim, Germany 193
27. R.J. Goodfellow, P.L. Goggin, and L.M. Venanzi J. Chem. Soc. A 1967 1897 1900
28. U. Kiehne, T. Weilandt, and A. Lützen Org. Lett. 9 2007 1283 1286
29. T. Weilandt, U. Kiehne, J. Bunzen, G. Schnakenburg, and A. Lützen Chem. Eur. J. 16 2010 2418 2426
30. M. Oestreich M. Oestreich, The Mizoroki-Heck Reaction 2009 John Wiley & Sons, Ltd., Chichester United Kingdom 56 57
31. V.P. Böhm, and W.A. Herrmann Chem. Eur. J. 7 2001 4191 4197
32. C. Amatore, and A. Jutand Acc. Chem. Res. 33 2000 314 321
33. D.R. Anton, and R.H. Crabtree Organometallics 2 1983 855 859
34. J.A. Widegren, and R.G. Finke J. Mol. Catal. A 198 2003 317 341
35. W.A. Herrmann, C. Brossmer, K. Öfele, C.P. Reisinger, T. Priermeier, M. Beller, and H. Fischer Angew. Chem. Int. Ed. Engl. 34 1995 1844 1848
36. M. Larhed, and A. Hallberg J. Org. Chem. 61 1996 9582 9584
37. M.R. Buchmeiser, and K. Wurst J. Am. Chem. Soc. 121 1999 11101 11107
38. J.C. van Miltenburg, and J.A. Bouwstra J. Chem. Thermodyn. 16 1984 61 65
39. F. Bergmann, and D. Schapiro J. Org. Chem. 12 1947 57 66
40. L.-T. Chu, P.-C. Yu, B.-J. Wu, Y.-C. Liao, and C.-H. Chow Heterocycles 71 2007 165 173