Activation of hydrogen by palladium(O): Formation of the mononuclear dihydride complex trans-[Pd(H)2(IPr)(PCy3)]

Angewandte Chemie - International Edition

Volumn 48, Issue 28, 2009, Pages 5182-5186

  Fantasia, Serena ^b,f   Egbert, Jonathan D ^a   Jurčík, Václav ^b,c   Cazin, Catherine S J ^b,c   Jacobsen, Heiko ^d   Cavallo, Luigi ^e   Heinekey, D Michael ^a   Nolan, Steven P ^b,c  

^a UNIVERSITY OF WASHINGTON   (United States)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c UNIVERSITY OF ST ANDREWS   (United Kingdom)

^d KemKom   (United States)

^e UNIVERSITY OF SALERNO   (Italy)

^f LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

Author keywords

Carbenes; Homogeneous catalysis; Hydrides; Hydrogen; Palladium

Indexed keywords

CARBENES; DENSITY-FUNCTIONAL CALCULATIONS; DIHYDRIDE COMPLEXES; DIHYDRIDES; H-BONDS; HOMOGENEOUS CATALYSIS; MULTINUCLEAR NMR SPECTROSCOPY; NEW SPECIES; SHARP CONTRAST; X-RAY DIFFRACTION STUDIES;

CATALYSIS; HYDRIDES; HYDROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; REACTION KINETICS; TRANSITION METAL COMPOUNDS;

PALLADIUM COMPOUNDS;

EID: 70349925406     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900463     Document Type: Article

References (86)

1. a) Handbook of Homogeneous Hydrogenation (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007.
2. b) B. Chen, U. Dingerdissen, J. G. E. Krauter, H. G J. Lansink Rotgerink, K. Moebus, D. J. Ostgard, P. Panster, T. H. Riermeier, S. Seebald, T. Tacke, H. Trauthwein, Appl. Catal. A 2005,280,.1.746.
3. c) H.-U Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151.
4. d) S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, Chichester, UK, 2001.
5. For a review on Wilkinson's catalyst, see : F. H. Jardine, Prog. Inorg. Chem. 1981, 28, 63-202.
6. a) A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Hörmann, S. Mclntyre, F. Menges, M. Schönleber, S. R Smidt, IB. Wüstenberg, N. Zimmermann, Adv. Synth. Catal. 2003, 345, 33-43.
7. b) R. H. Crabtree, Acc. Chem. Res. 1979, 72, 331-337.
8. a) P. Pelagatti, A. Bacchi, M. Carcelli, M. Costa, A. Fochi, R Ghidini, E. Leporati, M. Masi, C. Pelizzi, G. Pelizzi, J. Organomet. Chem. 1999, 583, 94-1.05.
9. b) P. Pelagatti, A. Venturini, A. Leporati, M. Carcelli, M. Costa, A. Bacchi, G. Pelizzi, C. Pelizzi, J. Chem. Soc. Dalton Trans. 1998,2715-2722.
10. c) V. V. S. Reddy, J. Mol. Catal. 1988, 45, 73-84.
11. d) M. M. Taqui Khan, B. Taqui Khan, S. Begum, J. Mol. Catal. 1988, 45, 305-317.
12. e) D. R. Armstrong, O. Novaro, M. E. Ruiz-Vizcaya, R. Linarte, J. Catal. 1977,48,8-20.
13. f) G. Carturan, G. Strukul, J. Organomet. Chem. 1978, 757,475-481.
14. g) G. H. Olivé, S. Olivé, J. Mol. Catal. 1975, 7,121-135.
15. h) G. Henrici-Olivé, S. Olivé, Angew. Chem. 1974, 86, 561-562;
16. Angew. Chem Int. Ed Engl. 1974, 75, 549-550.
17. i) For an early review see: F. R. Hartley, Chem. Rev. 1969, 69, 799-844.
18. 0 cluster-mediated hydrogenation, see: I.I. Moiseev, M. N. Vargaftik, New J. Chem. 1998, 22, 1217-1227.
19. b) R. van Asselt, C. J. Elsevier, J. Mol. Catal. 1991,65, L13-L19.
20. c) R. U. Kirss, R. Eisenberg, Inorg. Chem. 1989,28, 3372-3378.
21. d) E. W. Stern, P. K. Maples, J. Catal. 1972, 27, 120-133.
22. e) Y. Takahashi, Ts. Ito, S. Sakai, Y. Ishii, J. Chem. Soc. D1970, 1065-1066.
23. a) L. Andrews, X. Wang, M. E. Alikhani, L. Manceron, J. Phys. Chem. A 2001, 105, 3052-3063.
24. b) L. Andrews, L. Manceron, M. E. Alikhani, X. Wang, J. Am. Chem. Soc. 2000, 122, 11011-11012.
25. c) G A. Ozin, J. Garcia-Prieto, J. Am. Chem. Soc. 1986, 108, 3099-3100.
26. d) C. Jarque, O. Novaro, M. E. Ruiz, J. GarciaPrieto, J. Am. Chem. Soc. 1986, 108, 3507-3509.
27. e) X J. Low, W. A. Goddard III, J. Am. Chem. Soc. 1984, 106, 8321-8322.
28. f) J. R Coliman, Ace Chem. Res. 1968,1, 136-143.
29. g) R. Ugo, Coord Chem. Rev. 1968,5, 319-344.
30. h) S. Carra, R. Ugo, Inorg. Chim. Acta 1967, 7, 49-63.
31. i) J. Halpern, Adv. Catal. 1959, 77, 301-344.
32. j) J. Halpern, J. Phys Chem. 1959,63, 398-403.
33. a) M. W. van Laren, C. J. Elsevier, Angew. Chem. 1999, 777, 3926-3929;
34. Angew. Chem. Int. Ed. 1999, 38, 3715-3717.
35. b) C. Borriello, M. L. Ferrara, I. Orabona, A. Panunzi, F. Ruffo, J. Chem. Soc. Dalton Trans. 2000,2545-2550.
36. c) M. W. van Laren, M. A. Duin, C. Klerk, M. Naglia, D. Rogolino, R Pelegatti, A. Bacchi, C. Pelizzi, C. J. Elsevier, Organometallics 2002,21,15461553.
37. d) D. Evrard, K. Groison, Y. Mugnier, R D. Harvey, Inorg. Chem. 2004,43,790-796.
38. e) J. W. Sprengers, J. Wassenaar, N D. Clement, K.J. Cavell, C. J. Elsevier, Angew. Chem. 2005, 777, 2062-2065;
39. Angew. Chem. Int. Ed. 2005, 44, 2026-2029.
40. f) H. Guo, Z. Zheng, F. Yu, S. Ma, A. Holuigue, D. S. Tromp, C. J. Elsevier, Y. Yu, Angew. Chem 2006, 118, 5119-5122;
41. Angew. Chem. Int. Ed. 2006, 45, 4997-50(K).
42. g) H. Sajiki, S. Mori, T. Ohkubo, T. Ikawa, A. Kume, T. Maegawa, Y. Monguchi, Chem. Eur. J. 2008, 14, 5109-5111.
43. h) P. Hauwert, G. Maestri, J. W. Sprengers, M. Catellani, C. J. Elsevier, Angew. Chem. 2008, 720, 3267-3270.
44. Angew. Chem. Int. Ed. 2008,47,3223-3226.
45. a) A. M. Kluwer, T. S. Koblenz, T. Jonischkeit, K. Woelk, C. J. Elsevier, J. Am. Chem. Soc. 2005, 727, 15470-15480.
46. b) J. López-Serrano, S. B. Duckett, S. Aiken, K. Q. Almeida Leñero, E. Drent, J, P. Dunne, D. Konya, A. C. Whitwood, J. Am. Chem. Soc. 2007,729, 6513-6527.
47. 3 is disclosed. The complex was characterized solely by IR spectroscopy, see : K. Kudo, M. Hidai, Y. Uchida, J. Organomet. Chem. 1973, 56, 413-418.
48. G S. McGrady, G. Guilera, Chem. Soc. Rev. 2003, 32, 383-392, and references therein.
49. a) M. D. Fryzuk, B. R. Lloyd, G. K. B. Clentsmith, S. J. Rettig, J. Am. Chem. Soc. 1994, 116, 3804-3812.
50. b) S. Chan, W-T Wong, J. Chem. Soc. Dalton Trans. 1995,3987-3994.
51. c) J. W-S. Hiu, WT Wong, J. Chem. Soc. Dalton Trans. 1997, 1515-1520.
52. d) S. Kuwata, S. Kabashima, Y. Ishii, M. Hidai, J. Am. Chem. Soc. 2001, 725, 3826-3827.
53. e) S. Du, J. C. Jeffery, J. A. Kautz, X. L. Lu, T. D. McGrath, T. A. Miller, T. Riis-Johannessen, F. G. A. Stone, Inorg. Chem. 2005, 44, 2815-2825.
54. N. M. Scott, S. P. Nolan, Eur. J. Inorg. Chem. 2005, 1815-1828.
55. S. Fantasia, S. R Nolan, Chem Eur. J. 2008,14, 6987-6993.
56. V Jurčík, S. P. Nolan, C. S. J. Cazin, Chem. Eur. J. 2009,75,25092511.
57. For more details, see the Supporting Information.
58. trans J(RH) coupling constants are usually > 160 Hz, whereas for cis couplings, values are 0-20 Hz;
59. for selected examples, see: a) IB. Kellenberger, S. J. Young, J. K. Stille, J. Am. Chem. Soc. 1985, 107, 6105-6107.
60. b) R Leoni, M. Sommovigo, M. Pasquali, S. Midollini, D. Braga, R Sabatino, Organometallics 1991, 10, 1038-1044.
61. c) K. Schager, K. Seevogel, K-R. Pörschke, M. Kessler, C. Krüger, J. Am. Chem. Soc. 1996, 118,13075-13076.
62. d) R J. Pérez, J. C. Calabrese, E. B. Bunel, Organometallics 2001, 20, 337-345.
63. e) O. V. Ozerov, C. Guo, L. Fan, B. M. Foxman, Organometallics 2004,23, 5573-5580.
64. f) I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126,13178-13179.
65. a) P. J. Desrosiers, L. Cai, Z. Lin, R. Richards, J. Halpern, J. Am. Chem. Soc. 1991, 113, 4173-4184.
66. b) C. A. Bayse, R. L. Luck, E. J. Schelter, Inorg. Chem. 2001, 40, 3463-3467.
67. V. V. Grushin, Chem. Rev. 1996, 96, 2011-2033.
68. a) N. D. Clement, K. J. Cavell, C. Jones, C. J. Elsevier, Angew. Chem. 2004, 116, 1297-1299;
69. Angew. Chem. Int. Ed. 2004, 43, 1277-1279.
70. b) M. M. Konnick, B. A. Gandhi, I. A. Guzei, S. S. Stahl, Angew. Chem. 2006, 118, 2970-2973;
71. Angew. Chem. Int. Ed. 2006,45, 2904-2907.
72. a) D. S. McGuinness, K. J. Cavell, B. W. Skelton, A. H. White, Organometallics 1999,18, 1596-1605.
73. b) R L. Arnold, F. G. N. Cloke, T. Geldbach, P. B. Hitchcock, Organometallics 1999,18, 3228-3233.
74. 13).
75. 2). See: a) R. H. Morris, J. F. Sawyer, M. Shiralian, J. D. Zubkowski, J. Am Chem. Soc. 1985, 107, 5581-5582.
76. b) G. J. Kubas, R. R. Ryan, B. I. Swanson, R J. Vergamini, H. J. Wasserman, J. Am. Chem. Soc. 1984, 108, 451-452.
77. 2 transition-metal complexes are in the range 30-35 Hz, whereas for complexes containing hydride and deutende ligands, J. (H,D) < 3 Hz. The slightly higher value detected in our case might be a result of the trans geometry, see for example: a) G J. Kubas, C. J. Unkefer, B. I. Swanson, E. Fukushima, J. Am. Chem. Soc. 1986, 108, 7000-7009.
78. b) G.X Kubas, R. R. Ryan, D. A. Wrobleski, J. Am. Chem. Soc. 1986, 108, 1339-1341,
79. c) R. Gelabert, M. Moreno, J. M. Lluch, A. Lledos, V. Pons, D. M. Heinekey, J. Am. Chem. Soc. 2004, 126, 8813-8822, and references therein.
80. a) S. Diez-González, S. R Nolan, Coord. Chem. Rev. 2007, 257, 874-883.
81. b) H. Jacobsen, A. Correa, A. Poater, C. Costabile, L. Cavallo, Coord. Chem. Rev. 2009, 253, 687-703.
82. c) F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216; Angew.
83. Chem. Int. Ed. 2008, 47, 3122-3172.
84. d) R de Fremont, N. Marion, S. R Nolan, Coord. Chem. Rev. 2009,253, 862-892.
85. C. A. Tolman, Chem. Rev. 1977, 77, 313-348.
86. V. V. Grushin, C. Bensimon, H. Alper, Inorg. Chem. 1994, 33, 4804-4806.