Highly efficient pyridylpyrazole ligands for the heck reaction. A combined experimental and computational study

Organometallics

Volumn 27, Issue 6, 2008, Pages 1084-1091

  Montoya, Vanessa ^a   Pons, Josefina ^a   Branchadell, Vicenç ^a   Garcia Antón, Jordi ^a   Font Bardía, Mercè ^b   Ros, Josep ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; SOLVENTS;

CHLOROBENZENE; PHENYL HALIDES; PYRIDYLPYRAZOLE;

LIGANDS;

EID: 41749083301     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7009182     Document Type: Article

References (55)

1. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, UK, 1985.
2. Heck, R. F. Pure Appl. Chem. 1978, 50, 691.
3. Heck, R. F. Acc Chem. Res. 1979, 12, 146.
4. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
5. Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283.
6. Heck, R. F. In Comprensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol 4.
7. De Meijere, A.; Braese, S. In Transition Metal Catalyzed Reactions; Davies, S. G., Murahashi; S. I., Eds.; Blackwell Science: Oxford, UK, 1999.
8. Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
9. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev 2000, 100, 3009.
10. Herrmann, W. A.; Ofele, K.; von Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229.
11. Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
12. Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608.
13. Deeth, R. J.; Smith, A.; Hii, K. K.; Brown, J. M. Tetrahedron Lett. 1999, 39, 3229.
14. Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim. Acta 2001, 84, 3043.
15. von Schenck, H.; Strömberg, S.; Zetterberg, K.; Ludwig, M.; Åkermark, B.; Svensson, M. Organometallics 2001, 20, 2813.
16. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem.-Eur. J. 2001, 7, 1703.
17. von Schenck, H.; Åkermark, B.; Svensson, M. Organometallics 2002, 27, 2248.
18. von Schenck, H.; Åkermark, B.; Svensson, M. J. Am. Chem. Soc. 2003, 125, 3503.
19. Lin, B. L.; Liu, L.; Fu, Y.; Luo, S. W.; Chen, Q.; Guo, Q. X. Organometallics 2004, 23, 2114.
20. Balcells, D.; Maseras, F.; Keay, B. A.; Ziegler, T. Organometallics 2004, 23, 2784.
21. Deeth, R. J.; Smith, A.; Brown, J. M. J. Am. Chem. Soc. 2004, 126, 7144.
22. Datta, G. K.; von Schlenk, H.; Hallberg, A.; Larhed, M. J. Org. Chem. 2006, 7, 3896.
23. Lee, M. T.; Lee, H. M.; Hu, C. H. Organometallics 2007, 26, 1317.
24. Casabó, J.; Pons, J.; Siddiqi, K. S.; Teixidor, F.; Molins, E.; Miravitlles, C. J. Chem. Soc., Dalton Trans. 1989, 1401.
25. Chadghan, A.; Pons, J.; Caubet, A.; Casabó, J.; Ros, J.; Alvarez-Larena, A.; Pinieila, J. F. Polyhedron 2000, 19, 855.
26. Perez, J. A.; Pons, J.; Solans, X.; Font-Bardia, M.; Ros, J. Inorg. Chim. Acta 2005, 358, 617.
27. Thiel, W. R.; Eppinger, J. Chem. - Eur. J 1997, 3, 696.
28. Montoya, V.; Pons, J.; Garcia-Antón, J.; Solans, X.; Font-Bardia, M.; Ros, J. Inorg. Chim. Acta 2007, 360, 625.
29. Montoya, V.; Pons, J.; Branchadell, V.; Ros, J. Tetrahedron, 2005, 61, 12377.
30. Montoya, V.; Pons, J.; Solans, X.; Font-Bardia, M.; Ros, J. Inorg. Chim. Acta 2006, 359, 25.
31. Montoya, V.; Pons, J.; Garcia-Anton, J.; Solans, X.; Font-Bardia, M.; Ros, J. Organometallics 2007, 26, 3183.
32. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317.
33. Najera, C.; Gil-Moltó, J.; Karlström, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
34. Perez, J. A. Thesis, 2003.
35. Synthesis of Organometallic Compounds: a Practice Guide; Komiya, S., Ed.; Wiley: New York, 1997.
36. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
37. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
38. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
39. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
40. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
41. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry, Vol. 3; Schaeffer, H. F., Ill, Ed.; Plenum: New York, 1976; p 1.
42. Standard exponents were used for C (0.75), N (0.80), O (0.85), Cl (0.60), and Br (0.338). The exponent for I (0.266) has been taken from: Huzinaga, S.; Andzelm, J.; Klobukowski, M.; Radzio-Andzelm, E.; Sakai, Y.; Tatewaki, H. Gaussian Basis Sets for Molecular Calculations; Elsevier: Amsterdam, 1984.
43. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 1993, 2, 799.
44. (b) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
45. (c) Cossi, Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
46. Standard exponents were used for C (0.0438), N (0.0639), O (0.0845), Cl (0.0483), and Br (0.035). The exponent for 1 (0.0368) was optimized for the atomic ground-state anion by Ted Packwood at NDSU. Diffuse functions for this and other heteroatoms may be found at the Web site: http://www.msg.ameslab.gov/ gamess/documentation.html.
47. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004, http://www.gaussian.com.
48. (a) te Velde, T. G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C; van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931.
49. (b) ADF200501, SCM, Theoretical Chemistry, Vrije Universiteit: Amsterdam, The Netherlands, http://www.scm.com.
50. Watson, M. A.; Handy, N. C.; Cohen, A. J. J. Chem. Phys. 2003, 119, 6475.
51. (a) van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1993, 99, 4597.
52. (b) van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1994, 101, 9783.
53. (c) van Lenthe, E.; Snijders, J. G.; Baerends, E. J. J. Chem. Phys. 1996, 105, 6505.
54. (d) van Lenthe, E.; van Leeuwen, R.; Baerends, E. J.; Snijders, J. G. Int. J Quantum Chem. 1996, 57, 281.
55. van Lenthe, E.; Ehlers, A. E.; Baerends, E. J. J. Chem. Phys. 1999, 110, 8943.