An anion-dependent switch in selectivity results from a change of C-H activation mechanism in the reaction of an imidazolium salt with IrH 5(PPh3)2

Journal of the American Chemical Society

Volumn 127, Issue 46, 2005, Pages 16299-16311

  Appelhans, Leah N ^a   Zuccaccia, Daniele ^b   Kovacevic, Anes ^a   Chianese, Anthony R ^a   Miecznikowski, John R ^a   Macchioni, Alceo ^b   Clot, Eric ^c   Eisenstein, Odile ^c   Crabtree, Robert H ^a  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF PERUGIA   (Italy)

^c UNIV MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; COMPUTATIONAL METHODS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PROTONS; REACTION KINETICS;

ANION DEPENDENCE; COMPUTATIONAL WORK; PROTON TRANSFER; REACTION PRODUCTS;

IRIDIUM COMPOUNDS;

2 PYRIDYLMETHYLIMIDAZOLIUM; ANION; ANTIMONY DERIVATIVE; BORON TRIFLUORIDE; BROMIDE; CARBON; FLUOROPHOSPHATE; HYDROGEN; IMIDAZOLE; IMIDAZOLE DERIVATIVE; IRIDIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ANION TRANSPORT; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; MATHEMATICAL COMPUTING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON TRANSPORT;

EID: 28044454126     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055317j     Document Type: Article

References (73)

1. Macchioni, A. Chem. Rev. 2005, 105, 2039 and references therein.
2. Bellachioma, G.; Cardaci, G.; Macchioni, A.; Reichenbach, G.; Terenzi, S. Organometallics 1996, 15, 4349.
3. Macchioni, A.; Bellachioma, G.; Cardaci, G.; Gramlich, V.; Rüegger, H.; Terenzi, S.; Venanzi, L. M. Organometallics 1997, 16, 2139.
4. Macchioni, A. Eur. J. Inorg. Chem. 2003, 195.
5. Macchioni, A.; Zuccaccia, C.; Clot, E.; Gruet, K.; Crabtree, R. H. Organometallics 2001, 20, 2367.
6. Gruet, K.; Clot, E.; Eisenstein, O.; Lee, D.-H.; Patel, B.; Macchioni, A.; Crabtree, R. H. New J. Chem. 2003, 27, 80.
7. Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntrye, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
8. Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165.
9. Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 373.
10. Basallote, M. G.; Besora, M.; Durán, J.; Fernández- Trujillo, M. J.; Lledós, A.; Máñez, M. A.; Maseras, F. J. Am. Chem. Soc. 2004, 126, 2320.
11. Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201.
12. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
13. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
14. Herrmann, W. A.; Reisinger, C. P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93.
15. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1291.
16. Ho, V. M.; Watson, L. A.; Huffman, J. C.; Caulton, K. G. New J. Chem. 2003, 27, 1446.
17. Grudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247.
18. Cavell, K. J.; McGuinness, D. S. Coord. Chem. Rev. 2004, 248, 671.
19. Kovacevic, A.; Gründemann, S.; Miecznikowski, J. R.; Clot, E.; Eisenstein, O.; Crabtree, R. H. Chem. Commun. 2002, 2580.
20. Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R.; Szemes, F.; Drew, M. G. B. J. Am. Chem. Soc. 2005, 127, 2292 and references therein.
21. Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
22. Danopoulos, A. A.; Tsoureas, N.; Wright, J. A.; Light, M. E. Organometallics 2004, 23, 166.
23. Hu, X.; Castro-Rodriguez, I.; Meyer, K. Organometallics 2003, 22, 3016.
24. (a) McGuinness, D. S.; Cavell, K. J.; Yates, B. F.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 2001, 123, 8317.
25. (b) McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029.
26. (c) Gründemann, S.; Albrecht, M.; Kovacevic, A.; Faller, J. W.; Crabtree, R. H. Dalton Trans. 2002, 2163.
27. Viciano, M.; Mas-Marza, K.; Poyatos, M.; Sanau, M.; Crabtree, R. H.; Peris, E. Angew. Chem., Int. Ed. 2005, 44, 444.
28. Frenking, G.; Frohlich, N. Chem. Rev. 2000, 100, 717.
29. Dorta, R.; Stevens, E. D.; Scott, N. M.; Costabile, C.; Cavallo, E.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 2485.
30. Perrin, E.; Clot, E.; Eisenstein, O.; Loch, J.; Crabtree, R. H. Inorg. Chem. 2001, 40, 5806.
31. Baba, E.; Cundari, T. R.; Firkin, I. Inorg. Chim. Acta 2005, 358.
32. Mungur, S. A.; Liddle, S. T.; Wilson, C.; Sarsfield, M. J.; Arnold, P. J. Chem. Commun. 2004, 2738.
33. Hu, X. L.; Caxtro-Rodriguez, I.; Olsen, K.; Meyer, K. Organometallics 2004, 23, 755.
34. Green, J. C.; Herbert, B. J. Dalton Trans. 2005, 1214.
35. Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277.
36. McGuiness, D. S.; Cavell, K. J.; Yates, B. F. Chem. Commun. 2001, 355.
37. Rivera, G.; Crabtree, R. H. J. Mol. Catal. A 2004, 222, 59.
38. Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. J. Am. Chem. Soc. 2002, 124, 10473.
39. Smidt, S. P.; Zimmermann, N.; Studer, M.; Pfaltz, A. Chem.-Eur. J. 2004, 10, 4685.
40. Cowan, J. A.; Clyburne, J. A. C.; Davidson, M. G.; Harris, R. L. W.; Howard, J. A. K.; Küpper, P.; Leech, M. A.; Richards, S. P. Angew. Chem., Int. Ed. 2002, 41, 1432.
41. (a) Hahn, E. L. Phys. Rev. 1950, 80, 580.
42. (b) Stejskal, E. O.; Tanner, J. E. J. Chem. Phys. 1965, 42, 288.
43. (c) Stilbs, P. Prog. Nucl. Magn. Reson. Spectrosc. 1987, 19, 1.
44. (d) Price, W. S. Concepts Magn. Reson. 1997, 9, 299.
45. (e) Price, W. S. Concepts Magn. Reson. 1998, 10, 197.
46. (f) Johnson, C. S., Jr. Prog. Nucl. Magn. Reson. Spectrosc. 1999, 34, 203.
47. For reviews on applications to organometallic chemistry, see: (a) Valentini, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833.
48. (b) Binotti, B.; Macchioni, A.; Zuccaccia, C.; Zuccaccia, D. Comments Inorg. Chem. 2002, 23, 417.
49. (c) Pregosin, P. S.; Martinez-Viviente, E.; Kumar, P. G. A. Dalton Trans. 2003, 4007.
50. N refers to the hydride trans to pyridine in the product of C-H activation: see Table 2.
51. Chianese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics 2004, 23, 2461.
52. Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. Chem. Commun. 2001, 2274.
53. Kubas, G. J. Metal Dihydrogen and σ-Bond Complexes: Structure. Theory and Reactivity, Kluwer Academic Publishers: New York, 2001.
54. Crabtree, R. H.; Felkin, H.; Morris, G. E. J. Orsganomet. Chem. 1977, 141, 205.
55. McGuiness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741.
56. Crabtree, R. H.; Demou, P. C.; Eden, D.; Mihelcic, J. M.; Parnell, C. A.; Quirk, J. M.; Morris, G. E. J. Am. Chem. Soc. 1982, 104, 6994.
57. Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
58. Wagner, R.; Berger, S. J. Magn. Reson., Ser. A 1996, 123, 119.
59. Lix, B.; Sönnichsen, F. D.; Sykes, B. D. J. Magn. Reson., Ser. A 1996, 121, 83.
60. Zuccaccia, D.; Macchioni, A. Organometallics 2005, 24, 3476.
61. Tulloch, A. A. D.; Danopoulos, A. A.; Winston, S.; Kleinhenz, S.; Eastham, G. J. Chem. Soc., Dalton Trans. 2000, 4499.
62. Pople, J. A.; et al. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA. 1998.
63. Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357.
64. Rappé, A. K.; Casewitt, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
65. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
66. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
67. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
68. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
69. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuß, H. Theor. Chim. Acta 1990, 77, 123.
70. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuß, H. Mol. Phys. 1993, 30, 1431.
71. 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.
72. Höllwarth, A.; Böhme, H.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
73. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.