Neutral ligands with exceptional donor ability for palladium-catalyzed alkene hydrogenation

Angewandte Chemie - International Edition

Volumn 46, Issue 33, 2007, Pages 6293-6296

  Heckenroth, Marion ^a   Kluser, Evelyne ^a   Neels, Antonia ^b   Albrecht, Martin ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

^b UNIVERSITY OF NEUCHÂTEL   (Switzerland)

Author keywords

Bonding modes; Cyclometalation; Hydrogenation; N heterocyclic carbenes; Palladium

Indexed keywords

BONDING; CATALYST ACTIVITY; HYDROGENATION; LIGANDS; PALLADIUM COMPOUNDS;

BONDING MODES; CARBENE; CYCLOMETALATION; DONOR ABILITY;

OLEFINS;

EID: 34548216695     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702199     Document Type: Article

References (50)

1. J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507;
2. R. H. Crabtree, Chem. Rev. 1995, 95, 987.
3. a) P. L. Watson, J. Am. Chem. Soc. 1983, 105, 6491;
4. b) M. E. Thompson, S. M. Baxter, A. R. Bulls, B. J. Burger, M. C. Nolan, B. D. Santarsiero, W. P. Schaefer, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 203;
5. c) J. Y. K. Tsang, M. S. A. Buschhaus, P. Legzdins, J. Am. Chem. Soc. 2007, 129, 5372.
6. a) A. E. Shilov, G. B. Shul'pin, Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes, Kluwer, Dordrecht, 2000;
7. b) "Activation and Functionalization of C-H Bonds": ACS Symp. Ser. 2004, 885 (Eds.: K. I. Goldberg, A. S. Goldman).
8. R. A. Periana, D. J. Taube, S. Gamble, H. Taube, T. Satoh, H. Fujii, Science 1998, 280, 560.
9. a) R. G. Bergman, Science 1984, 223, 902;
10. b) C. M. Jensen, Chem. Commun. 1999, 2443;
11. c) I. Göttker-Schnetmann, P. White, M. Brookhart, J. Am. Chem. Soc. 2004, 126, 1804.
12. a) D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39;
13. b) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
14. Angew. Chem. Int. Ed. 2002, 41, 1290;
15. c) N-Heterocyclic Carbenes in Synthesis (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006.
16. a) V. Lavallo, J. Mafhouz, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 8670;
17. b) V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851;
18. Angew. Chem. Int. Ed. 2005, 44, 5705;
19. c) V. Lavallo, Y. Canac, A. Dehope, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 7402;
20. Angew. Chem. Int. Ed. 2005, 44, 7236.
21. a) J. S. Owen, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2004, 126, 8247;
22. b) W. H. Meyer, M. Deetlefs, M. Pohlmann, R. Scholtz, M. W. Esterhuysen, G. R. Julius, H. G. Raubenheimer, Dalton Trans. 2004, 413;
23. c) M. Albrecht, H. Stoeckli-Evans, Chem. Commun. 2005, 4705;
24. d) S. K. Schneider, G. R. Julius, C. Loschen, H. G. Raubenheimer, G. Frenking, W. A. Herrmann, Dalton Trans. 2006, 1226;
25. e) S. K. Schneider, P. Roembke, G. R. Julius, H. G. Raubenheimer, W. A. Herrmann, Adv. Synth. Catal. 2006, 348, 1862.
26. a) S. Gründemann, A. Kovacevic, M. Albrecht, J. W. Faller, R. H. Crabtree, J. Am. Chem. Soc. 2002, 124, 10 473;
27. b) A. R. Chianese, A. Kovacevic, B. M. Zeglis, J. W. Faller, R. H. Crabtree, Organometallics 2004, 23, 2461;
28. c) H. Lebel, M. K. Janes, A. B. Charette, S. P. Nolan, J. Am. Chem. Soc. 2004, 126, 5046;
29. d) D. Bacciu, K. J. Cavell, I. A. Fallis, L. Ooi, Angew. Chem. 2005, 117, 5416;
30. Angew. Chem. Int. Ed. 2005, 44, 5282;
31. e) J. Schütz, E. Herdtweck, W. A. Herrmann, Organometallics 2004, 23, 6084.
32. W. A. Herrmann, J. Schwarz, M. G. Gardiner, Organometallics 1999, 18, 4082.
33. See the Supporting Information for details of the X-ray crystal structures of 2b and 4 and of the catalytic experiments.
34. M. Heckenroth, A. Neels, H. Stoeckli-Evans, M. Albrecht, Inorg. Chim. Acta 2006, 359, 1929.
35. a) W. A. Herrmann, J. Schwarz, M. G. Gardiner, M. Spiegler, J. Organomet. Chem. 1999, 575, 80;
36. b) A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. White, D. J. Williams, A. H. White, B. W. Skelton, J. Organomet. Chem. 2001, 617, 546;
37. c) S. Ahrens, A. Zeller, M. Taige, T. Strassner, Organometallics 2006, 25, 5409;
38. d) T. Scherg, S. K. Schneider, G. D. Frey, J. Schwarz, E. Herdtweck, W. A. Herrmann, Synlett 2006, 2894.
39. A structure search of the CSD returned only one compound with shorter Ag⋯Pd interactions: a) Y. Liu, K. H. Lee, J. J. Vittal, T. S. A. Hor, J. Chem. Soc. Dalton Trans. 2002, 2747;
40. see also: b) J. Forniés, A. Martin in Metal Clusters in Chemistry, Vol. 1 (Eds.: P. Braunstein, L. A. Oro, P. R. Raithby), Wiley-VCH, Weinheim, 1999, p. 417.
41. C. D. Wagner, W. M. Riggs, L. E. Davis, J. E. Moulder in Handbook of X-ray Photoelectron Spectroscopy (Ed.: G. E. Mullenberg), Perkin-Elmer, Minnesota, 1979.
42. P. Pelagatti in Handbook of Homogeneous Hydrogenation, Vol. 1 (Eds.: G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007, p. 71.
43. [21]
44. G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2007, 316, 439.
45. D. S. McGuinness, M. J. Green, K. J. Cavell, B. W. Skelton, A. H. White, J. Organomet. Chem. 1998, 565, 165;
46. D. C. Graham, K. J. Cavell, B. F. Yates, Dalton Trans. 2006, 1768.
47. D. S. McGuinness, N. Saendig, B. F. Yates, K. J. Cavell, J. Am. Chem. Soc. 2001, 123, 4029.
48. a) J. Kiwi, M. Grätzel, J. Am. Chem. Soc. 1979, 101, 7214;
49. b) S. Klingenhöfer, W. Heitz, A. Greiner, S. Oestreich, S. Föster, M. Antonietti, J. Am. Chem. Soc. 1997, 119, 10 116;
50. c) J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667.