Cyclotrimerization reactions catalyzed by rhodium(I) half-sandwich complexes: A mechanistic density functional study

Organometallics

Volumn 26, Issue 15, 2007, Pages 3816-3830

  Orian, Laura ^a   Van Stralen, Joost N P ^b   Bickelhaupt, F Matthias ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; BENZENE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; ORGANOMETALLICS; POTENTIAL ENERGY SURFACES; RHODIUM COMPOUNDS;

CYCLOTRIMERIZATION; RHODACYCLE; TRANSITION STATES;

CATALYST ACTIVITY;

EID: 34547470497     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7004222     Document Type: Article

References (68)

1. (a) Jones, G. Pyridines and Their Benzoderivatives: Synthesis. In Comprehensive Heterocyclic Chemistry II; Katritzky, A., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, pp 167-243.
2. (b) Curran, D. P. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1994; Vols. 1-3.
3. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1985, 34, 259.
4. (a) The conversion of three acetylene molecules into benzene is kinetically prohibited: Dower, W. V.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1982, 104, 6878.
5. (b) The enthalpy of activation is responsible for the reluctance of acetylene to self-trimerize thermally: Houk, K. N.; Gandour, R. W.; Strozier, R. W.; Randon, N. G.; Paquette, L. A. J. Am. Chem. Soc. 1979, 101, 6797.
6. (c) Back, H. M. Can. J. Chem. 1971, 49, 2199.
7. (a) Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 280.
8. (b) Wakatsuki, Y.; Yamazaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 2715.
9. (a) Bönnemann, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 505.
10. (b) Bönnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248.
11. (a) Vollhardt, K. P. C. Acc. Chem. Res. 1977, 10, 1.
12. (b) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
13. (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
14. (b) Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787.
15. (c) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
16. (d) Kotha, S.; Brahmachar, E.; Lahni, K. Eur. J. Org. Chem. 2005, 4741.
17. Hardesty, J. H.; Koerner, J. B.; Albright, T. A.; Lee, G.-Y. J. Am. Chem. Soc. 1999, 121, 6055.
18. Gandon, V.; Agenet, N.; Vollhardt, P. C.; Malacria, M.; Aubert, C. J. Am. Chem. Soc. 2006, 128, 8509.
19. (a) Dehy, A. A; Koga, N. Bull. Chem. Soc. 2005, 78, 781.
20. (b) Dehy, A. A.; Suresh, C. H.; Koga, N. Bull. Chem. Soc. 2005, 78, 792.
21. Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003, 125, 11721.
22. Dazinger, G.; Torres-Rodrigues, M.; Kirchner, K.; Calhorda, M. J.; Costa, P. J. J. Organomet. Chem. 2006, 691, 4434.
23. Yamamoto, K.; Kinpara, K.; Saigoku, T.; Takagishi, H.; Okuda, S.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc 2005, 127, 605.
24. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
25. (b) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
26. (c) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
27. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
28. (a) te Velde, 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.
29. (b) Baerends, E. J.; et al. Computer code ADF2006.01; SCM, Theoretical Chemistry, Vrije Universiteit: Amsterdam, The Netherlands, 2006.
30. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799.
31. (b) Klamt, A. J. Phys. Chem. 1995, 99, 2224.
32. (a) Cioni, P.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Ronca, P. J. Mol. Catal. 1987, 40, 337.
33. (b) Diversi, P.; Ermini, L.; Ingrosso, G.; Lucherini, A. J. Organomet. Chem. 1993, 447, 291.
34. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
35. Rerek, M. E.; Ji, L.-N.; Basolo, F. J. Chem. Soc., Chem. Commun. 1983, 1208.
36. van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1994, 101, 9783.
37. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
38. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
39. (a) Bickelhaupt, F. M.; Baerends, E. J. Kohn-Sham density functional theory: Predicting and understanding chemistry. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers Inc.: New York, 2000; Vol. 15; p 1.
40. (b) Bickelhaupt, F. M.; Nibbering, N. M. M.; van Wezenbeek, E. M.; Baerends, E. J. J. Phys. Chem. 1992, 96, 4864.
41. (c) Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1.
42. (d) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558.
43. (a) de Jong, G. Th.; Solà, M.; Visscher, L.; Bickelhaupt, F. M. J. Chem. Phys. 2004, 121, 9982.
44. (b) de Jong, G. Th.; Geerke, D. P.; Diefenbach, A.; Bickelhaupt, F. M. Chem. Phys. 2005, 313, 261.
45. de Jong, G. Th.; Geerke, D. P.; Diefenbach, A.; Solà, M.; Bickelhaupt, F. M. J. Comput. Chem. 2005, 26, 1006.
46. de Jong, G. Th.; Bickelhaupt, F. M. J. Phys. Chem. A 2005, 109, 9685.
47. de Jong, G. Th.; Bickelhaupt, F. M. J. Chem. Theory Comput. 2006, 2, 322.
48. The slippage parameter A is defined as Δ = 1/2[(M-C1a + M-C3a) - (M-Cl+ M-C3)] where M-C1a and M-C3a are the longest distances between M and two adjacent C atoms of the Cp ring and M-C1 and M-C3 are the distances between M and the C atoms adjacent to C1a and C3a, respectively; in indenyl complexes C1a and C3a are the hinge C atoms.
49. Pye, C. C.; Ziegler, T. Theor. Chem. Acc. 1999, 101, 396.
50. Allinger, N. L.; Zhou, X.; Bergsma, J. J. Mol. Struct. (THEOCHEM) 1994, 312, 69.
51. Bon, R. S.; van Vliet, B.; Sprenkels, N. E.; Schmitz, R. F.; de Kanter, F. J. J.; Stevens, Chr. V.; Swart, M.; Bickelhaupt, F. M.; Groen, M. B.; Orra, R. V. A. J. Org. Chem. 2005, 70, 3542.
52. Veiros, L. F.; Dazinger, G.; Kirchner, K.; Calhorda, M. J.; Schmid, R. Chem.-Eur. J. 2004, 10, 5860.
53. Schore, N. E. Chem. Rev. 1988, 88, 1081.
54. Abdulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103.
55. (a) Ziegler, T.; Tschinke, V.; Fan, L.; Becke, A. D. J. Am. Chem. Soc. 1989, 111, 9177.
56. (b) Basolo, F. Coord. Chem. Rev. 1982, 43, 7.
57. (c) Janowicz, A. H.; Bryndza, H. E.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 1516.
58. (d) Cramer, R.; Seiwell, L. P. J. Organomet. Chem. 1975, 92, 245.
59. (e) Schuster-Woldan, H. G.; Basolo, F. J. Am. Chem. Soc. 1966, 88, 1657.
60. Wakatsuki, Y.; Nomura, O.; Kitaura, K.; Morokuma, K.; Yamazaki, H. J. Am. Chem. Soc. 1983, 105, 1907.
61. Schilling, B. E. R.; Hoffmann, R.; Lichtenberger, D. L. J. Am. Chem. Soc. 1979, 101, 585.
62. Bowyer, W. J.; Merkert, J. W.; Geiger, W. E.; Rheingold, A. L. Organometallics 1989, 8, 191.
63. Belt, S. T.; Helliwell, M.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. J. Am. Chem. Soc. 1993, 115, 1429.
64. Albano, V. G.; Braga, D.; Chini, P.; Martinengo, S.; Strumolo, D. Eur. Cryst. Meet. 1980, 6, 71.
65. Yamamoto, Y.; Kinpara, K.; Ogawa, R.; Nishiyama, H.; Itoh, K. Chem.-Eur. J. 2006, 12, 5618.
66. Caddy, P.; Green, M.; O'Brien, E.; Smart, L. E.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 962.
67. 2 bonding mode. In fact, the nodal properties of the Ind π system introduce an asymmetry that is not present in the Cp π orbitais: Calhorda, M. J.; Veiros, L. F. Coord. Chem. Rev. 1999, 185-186, 37. In addition slippage toward a more allylic coordination in Ind complexes favors the aromatic character of the benzene ring. As a consequence, the two bonds of the metal to the hinge carbons are longer and weaker and both the slippage parameter and the folding angle of the five-membered ring are more pronounced in Ind complexes than in the analogous Cp complexes. These structural features are commonly invoked to explain the higher reactivity of Ind complexes than Cp complexes ("indenyl effect").
68. Orian, L.; Bisello, A.; Santi, S.; Ceccon, A.; Saielli, G. Chem.-Eur. J. 2004, 10, 4029.