Structure, bonding, and dynamics of several palladium η3- allyl carbene complexes

Organometallics

Volumn 27, Issue 3, 2008, Pages 437-444

  Filipuzzi, Serena ^a   Pregosin, Paul S ^a   Albinati, Alberto ^a   Rizzato, Silvia ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL SHIFT; LIGANDS; TWO DIMENSIONAL;

CARBENE CARBON; CARBENE COMPLEXES; ELECTRONIC CONTROL;

PALLADIUM COMPOUNDS;

EID: 39649114103     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7010613     Document Type: Article

References (72)

1. (a) Arndt, S.; Schrock, R. R.; Mueller, P. Organometallics 2007, 26 (5), 1279-1290.
2. (b) Schrock, R. R. Adv. Synth. Catal. 2007, 349 (1+2), 25.
3. (c) Schrock, R. R. Adv. Synth. Catal. 2007, 349 (1+2), 41-53.
4. (d) Schrock, R. R.; Czekelius, C. Adv. Synth. Catal. 2007, 349 (1+2), 55-77.
5. (e) Grubbs, R. H. Adv. Synth. Catal. 2007, 349 (1+2), 23-24.
6. (f) Grubbs, R. H. Adv. Synth. Catal. 2007, 349 (1+2), 34-40.
7. (g) Mohapatra, D. K.; Ramesh, D. K.; Giardello, M. A.; Chorghade, M. S.; Gurjar, M. K.; Grubbs, R. H. Tetrahedron Lett. 2007, 48 (14), 2621-2625.
8. (h) Berlin, J. M.; Campbell, K.; Ritter, T.; Funk, T. W.; Chlenov, A.; Grubbs, R. H. Org. Lett. 2007, 9 (7), 1339-1342.
9. Douthwaite, R. E. Coord. Chem. Rev. 2007, 251 (5+6), 702-717.
10. Viciu, M. S.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. Organometallics 2003, 22 (16), 3175-3177.
11. Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21 (25), 5470-5472.
12. (a) Grundemann, S.; Albrecht, M.; Kovacevic, A.; Faller, J. W.; Crabtree, R. H. Z. Chem. Soc., Dalton Trans. 2002, (10), 2163-2167.
13. (b) Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21 (4), 700-706.
14. (c) Ketz, B. E.; Cole, A. P.; Waymouth, R. M. Organometallics 2004, 23 (12), 2835-2837.
15. (d) Bertogg, A.; Camponovo, F.; Togni, A. Eur. J. Inorg. Chem. 2005, (2), 347-356.
16. (e) Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem. Eur. J. 2006, 12 (19), 5142-5148.
17. (f) Amblard, F.; Nolan, S. P.; Schinazi, R. F.; Agrofoglio, L. A. Tetrahedron 2005, 61 (3), 537-544.
18. (g) Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7 (9), 1829-1832.
19. (a) Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251 (5-6), 874-883.
20. (b) Heckenroth, M.; Neels, A.; Stoeckli-Evans, H.; Albrecht, M. Inorg. Chim. Acta 2006, 359 (6), 1929-1938.
21. Chernyshova, E. S.; Goddard, R.; Poerschke, K.-R. Organometallics 2007, 26 (13), 3236-3251.
22. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23 (7), 1629-1635.
23. (a) Fuerstner, A.; Seidel, G.; Kremzow, D.; Lehmann, C. W. Organometallics 2003, 22 (5), 907-909.
24. (b) Furstner, A.; Krause, H.; Lehmann, C. W. Chem. Commun. 2001, (22), 2372-2373.
25. Vrieze, K. In Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975; p441-483.
26. (a) Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116 (9), 4067-4068.
27. (b) Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14 (7), 3311-3318.
28. (c) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35-68.
29. (d) Kumar, P. G. A.; Dotta, P.; Hermatschweiler, R.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2005, 24 (6), 1306-1314.
30. (a) Ogasawara, M.; Takizawa, K.; Hayashi, T. Organometallics 2002, 21 (22), 4853-4861.
31. (b) Cesarotti, E.; Grassi, M.; Prati, L.; Demartin, F. Z. Organomet. Chem. 1989, 370, 407-419.
32. (c) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36 (19), 2108-2110.
33. (d) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelein, M.; Huttner, G.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526.
34. (e) Crociani, B.; Antonaroli, S.; Bandoli, G.; Canovese, L.; Visentin, F.; Uguagliati, P. Organometallics 1999, 18 (7), 1137-1147.
35. (f) Faller, J. W.; Wilt, J. C. Organometallics 2005, 24 (21), 5076-5083.
36. (g) Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23 (9), 2008-2014.
37. Gogoll, A.; Ornebro, J.; Grennberg, H.; Bäckvall, J. E. J. Am. Chem. Soc. 1994, 116, 3631.
38. Kollmar, M.; Helmchen, G. Organometallics 2002, 21 (22), 4771-4775.
39. (a) Albinati, A.; Kunz, R. W.; Ammann, C. J.; Pregosin, P. S. Organometallics 1991, 10 (6), 1800-1806.
40. (b) Albinati, A.; Ammann, C.; Pregosin, P. S.; Ruegger, H. Organometallics 1990, 9 (6), 1826-1833.
41. Ding, Y.; Goddard, R.; Poerschke, K.-R. Organometallics 2005, 24 (3), 439-445.
42. -1 to the Pd-NCS isomer. This vibration is absent in our complex.
43. 13C NMR spectrum. Chem. Soc. Rev. 1999, 28, 95-105.
44. For one complex, X = CN, it was possible to resolve these meta-aryl carbene nonequivalent protons at 700 MHz (see Figure 2).
45. Shaw, B. L.; Mann, B. E.; Pietropaolo, R. Chem. Commun. 1971, (15), 790-791.
46. Boele, M. D. K.; Kamer, P. C. J.; Lutz, M.; Spek, A. L.; de Vries, J. G.; van Leeuwen, P.; van Strijdonck, G. P. E. Chem.-Eur. J. 2004, 10 (24), 6232-6246.
47. Krause, J.; Goddard, R.; Mynott, R.; Poerschke, K.-R. Organometallics 2001, 20 (10), 1992-1999.
48. Visentin, F.; Togni, A. Organometallics 2007, 26 (15), 3746-3754.
49. (a) Jaganyi, D.; Reddy, D.; Gertenbach, J. A.; Hofmann, A.; van Eldik, R. Dalton Trans. 2004, 2, 299-304.
50. (b) Hofmann, A.; Dahlenburg, L.; van Eldik, R. Inorg. Chem. 2003, 42 (20), 6528-6538.
51. Romeo, R.; Plutino, M. R.; Scolaro, L. M.; Stoccoro, S.; Minghetti, G. Inorg. Chem. 2000, 39 (21), 4749-4755.
52. We thank Mr. Pietro Butti for determining the structure. Details have been submitted to the Cambridge Database.
53. Roland, S.; Audouin, M.; Mangeney, P. Organometallics 2004, 23 (12), 3075-3078.
54. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123 (27), 6543-6554.
55. Fantasia, S.; Petersen, J. L.; Jacobsen, H.; Cavallo, L.; Nolan, S. P. Organometallics 2007, 26 (24), 5880-5889.
56. Fantasia, S.; Jacobsen, H.; Cavallo, L.; Nolan, S. P. Organometallics 2007, 26 (14), 3286-3288.
57. Cárdenas, D. J.; Echevarren, A. M.; Ramírez de Arellano, M. C. Organometallics 1999, 18, 3337-3341.
58. Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
59. We originally incorrectly assigned the restricted rotation to the Pd-C(carbene) bond. Restricted rotation of this type has been reported, but for t-butyl (and not i-Pr) substituents on the N-atom. (a) Burling, S.; Douglas, S.; Manon, M. F.; Nama, D.; Pregosin, P. S.; Whittlesey, M. K. Organometallics 2006, 25 (10), 2642-2648.
60. (b) Burling, S.; Paine, B. M.; Nama, D.; Brown, V. S.; Mahon, M. F.; Prior, T. J.; Pregosin, P. S.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2007, 129 (7), 1987-1995.
61. Zuccaccia, D.; Macchioni, A. Organometallics 2005, 24 (14), 3476-3486.
62. Led, J. J.; Gesmar, H. J. Magn. Reson. 1982, 49 (3), 444-463.
63. (a) The CIFIT program package was used for the simulations and data evaluation: Bain, A. D.; Cramer, J. A. J. Magn. Reson. Ser. A 1996, 118, 21.
64. (b) Muhandiram, D. R.; McClung, R. E. D. J. Magn. Reson. 1987, 71, 187.
65. (a) Pregosin, P. S.; Kumar, P. G. A.; Fernandez, I. Chem. Rev. 2005, 105 (8), 2977-2998.
66. (b) Pregosin, P. S. Prog. Nucl. Magn. Reson. Spectrosc. 2006, 49, 261-288.
67. BrukerAXS, SAINT, Integration Software; Bruker Analytical X-ray Systems: Madison, WI, 1995.
68. Sheldrick, G. M. SADABS, Program for Adsorption Correction; University of Göttingen: Göttingen, Germany, 1996.
69. Sheldrick, G. M. Shelx-97, Structure Solution and Refinement Package; Universitiy of Göttingen: Göttingen, Germany, 1997.
70. . International Tables for X-ray Cristallography; Kluwer Academic Publisher: Dordrecht, The Netherlands, 1992.
71. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
72. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.