Insight into the mechanism of R-R reductive elimination from the six-coordinate d6 complexes L2Pt(R)4 (R = vinyl, Me)

Organometallics

Volumn 30, Issue 3, 2011, Pages 422-432

  Ariafard, Alireza ^a   Ejehi, Zeinab ^a   Sadrara, Hoda ^a   Mehrabi, Tahmineh ^a   Etaati, Shohreh ^a   Moradzadeh, Azadeh ^a   Moshtaghi, Mahshid ^a   Nosrati, Hadis ^a   Brookes, Nigel J ^b   Yates, Brian F ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF TASMANIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATE COMPLEXES; ELECTRON-ACCEPTING; ELECTRON-DONATING; PRE-DISSOCIATION; REDUCTIVE ELIMINATION; SIX-COORDINATE COMPLEX;

DENSITY FUNCTIONAL THEORY; ELECTRONS; PLATINUM;

LIGANDS;

EID: 79751515020     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1005512     Document Type: Article

References (97)

1. Negishi, E. Palladium-Catalyzed Reactions Involving Reductive Elimination. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. I, p 213.
2. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3 rd ed.; John Wiley & Sons: New York, 2001.
3. Atwood, J. D. Inorganic and Organometallic Reaction Mechanisms, 2 nd ed.; Wiley-VCH: New York, 1997.
4. For theoretical investigations see: Ariafard, A.; Yates, B. F. J. Organomet. Chem. 2009, 694, 2075
5. Pérez-Rodríguez, M.; Braga, A. A. C.; Garcia-Melchor, M.; Prez-Temprano, M. H.; Casares, J. A.; Ujaque, G.; de Lera, A. R.; Álvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650
6. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Eur. J. Inorg. Chem. 2007, 5390
7. Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2006, 1768
8. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715
9. Zuidema, E.; van Leeuwen, P. W. N. M.; Bo, C. Organometallics 2005, 24, 3703
10. Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2005, 1093
11. McGuinness, D. S.; Yates, B. F.; Cavell, K. J. Organometallics 2002, 21, 5408
12. Low, J. J.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115
13. For experimental investigations see: Hartwig, J. F. Inorg. Chem. 2007, 46, 1936, and references therein
14. Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031, and references therein
15. Lindner, R.; Wagner, C.; Steinborn, D. J. Am. Chem. Soc. 2009, 131, 8861
16. Shahsavari, H. R.; Rashidi, M.; Nabavizadeh, S. M.; Habibzadeh, S.; Heinemann, F. W. Eur. J. Inorg. Chem. 2009, 3814
17. McBee, J. L.; Tilley, T. D. Organometallics 2009, 28, 3947
18. Zhao, S.-B.; Wang, R.-Y.; Wang, S. Organometallics 2009, 28, 2572
19. Smythe, N. A.; Grice, K. A.; Williams, B. S.; Goldberg, K. I. Organometallics 2009, 28, 277
20. Canty, A. J.; Watson, R. P.; Karpiniec, S. S.; Rodemann, T.; Gardiner, M. G.; Jones, R. C. Organometallics 2008, 27, 3203
21. Yahav-Levi, A.; Goldberg, K. I.; Vigalok, A.; Vedernikov, A. N. J. Am. Chem. Soc. 2008, 130, 724
22. Luedtke, A. T.; Goldberg, K. I. Inorg. Chem. 2007, 46, 8496
23. Pawlikowski, A. V.; Getty, A. D.; Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382.
24. Madison, B. L.; Thyme, S. B.; Keene, S.; Williams, B. S. J. Am. Chem. Soc. 2007, 129, 9538
25. Gallego, C.; Martínez, M.; Safont, V. S. Organometallics 2007, 26, 527
26. Yahav-Levi, A.; Goldberg, I.; Arkadi, V. J. Am. Chem. Soc. 2006, 128, 8710
27. West, N. M.; Reinartz, S.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 2006, 128, 2059
28. Zhang, F.; Prokopchuk, E. M.; Broczkowski, M. E.; Jennings, M. C.; Puddephatt, R. J. Organometallics 2006, 25, 1583
29. Prokopchuk, E. M.; Puddephatt, R. J. Organometallics 2003, 22, 787
30. Jensen, M. P.; Wick, D. D.; Reinartz, S.; White, P. S.; Templeton, J. L.; Goldberg, K. I. J. Am. Chem. Soc. 2003, 125, 8614
31. Prokopchuk, E. M.; Puddephatt, R. J. Organometallics 2003, 22, 563
32. Williams, B. S.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 2576
33. Reinartz, S.; White, P. S.; Brookhart, M.; Templeton, J. L. Organometallics 2000, 19, 3854
34. Williams, B. S.; Holland, A. W.; Goldberg, K. I. J. Am. Chem. Soc. 1999, 121, 252
35. Fekl, U.; Zahl, A.; van Eldik, R. Organometallics 1999, 18, 4156
36. Jenkins, H. A.; Yap, G. P. A.; Puddephat, R. J. Organometallics 1997, 16, 1946
37. Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966
38. Procelewska, J.; Zahl, A.; Liehr, G.; van Eldik, R.; Smythe, N. A.; Williams, B. S.; Goldberg, K. I. Inorg. Chem. 2005, 44, 7732
39. Arthur, K. L.; Wang, Q. L.; Bregel, D. M.; Smythe, N. A.; O'Neill, B. A.; Goldberg, K. I. Organometallics 2005, 24, 4624
40. Crumpton-Bregel, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2003, 125, 9442, and references therein.
41. Crumpton, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2000, 122, 962
42. Hill, G. S.; Yap, G. P. A.; Puddephatt, R. J. Organometallics 1999, 18, 1408
43. Hill, G. S.; Puddephatt, R. J. Organometallics 1997, 16, 4522
44. Goldberg, K. I.; Yan, J.; Breitung, E. M. J. Am. Chem. Soc. 1995, 117, 6889
45. Roy, S.; Puddephatt, R. J.; Scott, J. D. J. J. Chem. Soc., Dalton Trans. 1989, 2121
46. Brown, M. P.; Puddephatt, R. J.; Upton, C. E. E. J. Chem. Soc., Dalton Trans. 1974, 2457
47. Michel, C.; Milet, A. J. Mol. Struct. (THEOCHEM) 2008, 852, 54
48. Vastine, B. A.; Webster, C. E.; Hall, M. B. J. Chem. Theory Comput 2007, 3, 2268
49. 3 can undergo direct C-H elimination: Bartlett, K. L.; Goldberg, K. I.; Borden, T. Organometallics 2001, 20, 2669
50. Bartlett, K. L.; Goldberg, K. I.; Borden, T. J. Am. Chem. Soc. 2000, 122, 1456
51. Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478
52. See page 172 of ref 1b.
53. 6 six-coordinate complexes. Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857
54. Albright, T. A.; Burdett, J. K.; Whangbo, M.-H. Orbital Interactions in Chemistry; Wiley: New York, 1985; p 372.
55. Lin, Z.; Xue, L. Chem. Soc. Rev. 2010, 39, 1692
56. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 2839, and references therein
57. Frisch, M. J.; et al. Gaussian 09, revision A.02; Gaussian, Inc.: Pittsburgh, PA, 2009.
58. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785
59. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
60. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200
61. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
62. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
63. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
64. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213
65. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
66. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237
67. Metal-phosphine bond energies are underestimated by the B3LYP calculations: Sieffert, N.; Bühl, M. Inorg. Chem. 2009, 48, 4622
68. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364
69. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
70. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2006, 110, 13126
71. Yates, B. F. J. Mol. Struct. (THEOCHEM) 2000, 506, 223
72. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
73. 4 complex is much less reactive toward reductive elimination than the cis complex. Further details are provided in the Supporting Information.
74. Our calculations show that the inclusion of a molecule of the coordinating solvent acetonitrile does not affect the reductive elimination barriers predicted in Figures 1 and 2 (see the Supporting Information for detail; Figures S4 and S5).
75. 298 = 11.4 kcal/mol (see Figures 1 and S6). The energy difference between the δ H and δ G values (17.2 kcal/mol) is greater than the one suggested by Ziegler (8-12 kcal/mol) (see refs 27b, 27c, 27f), indicating an incorrect estimate of δ G from the gas phase calculation. A precise estimate of δ G in solution is too difficult to calculate. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647
76. Ziegler, T.; Vanka, K.; Xu, Z. C. R. Chim. 2005, 8, 1552
77. Yang, S.-Y.; Szabo, M. J.; Michalak, A.; Weiss, T.; Piers, W. E.; Jordan, R. F.; Ziegler, T. Organometallics 2005, 24, 1242
78. Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457
79. Sakaki, S.; Takayama, T.; Sumimoto, M.; Sugimoto, M. J. Am. Chem. Soc. 2004, 126, 3332
80. Kelly, E.; Seth, M.; Ziegler, T. J. Phys. Chem. A 2004, 108, 2176
81. Tamura, H.; Yamasaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114
82. Riehl, J.-F.; Yves, J.; Eisenstein, O.; Pélissier, M. Organometallics 1992, 11, 729
83. Our IRC calculation showed that the Y-type distorted trigonal-bipyramidal structure is not a local minimum for the vinyl system.
84. Wei, C. S.; Jiménez-Hoyos, C. A.; Videa, M. F.; Hartwig, J. F.; Hall, M. B. J. Am. Chem. Soc. 2010, 132, 3078
85. The entropic terms for experimental activation energies of Pt(IV)-L dissociation processes have been shown to vary from positive to negative values depending on the leaving group ligands and conditions. Bernhardt, P. V.; Gallego, C.; Martinez, M.; Parella, T. Inorg. Chem. 2002, 41, 1747
86. Esteban, J.; Font-Bardia, M.; Gallego, C.; González, G.; Martínez, M.; Solans, X. Inorg. Chim. Acta 2003, 351, 269
87. Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030
88. 2 can preferentially proceed through a direct pathway. For details see the Supporting Information. Ogasawara, M.; Macgregor, S. A.; Streib, W. E.; Folting, K.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1996, 118, 10189
89. 3 ligand.
90. Leyssens, T.; Peeters, D.; Orpen, A. G.; Harvey, J. N. Organometallics 2007, 26, 2637
91. Woska, D.; Prock, A.; Giering,l, W. P. Organometallics 2000, 19, 4629
92. Kraatz, H.-B.; Jacobsen, H.; Ziegler, T.; Boorman, P. M. Organometallics 1993, 12, 76
93. Ariafard, A. J. Organomet. Chem. 2004, 689, 2275
94. Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755
95. Bessac, F.; Frenking, G. Inorg. Chem. 2006, 45, 6956
96. Nemcsok, D. S.; Kovács, A.; Rayón, V. M.; Frenking, G. Organometallics 2002, 21, 5803
97. 3 has clearly the L dissociation prior to the reductive elimination whereby entropic considerations assist the reductive process.