Reaction of molecular oxygen with a PdII-hydride to produce a PdII-hydroperoxide: Acid catalysis and implications for Pd-catalyzed aerobic oxidation reactions

Angewandte Chemie - International Edition

Volumn 45, Issue 18, 2006, Pages 2904-2907

  Konnick, Michael M ^a   Gandhi, Bhavesh A ^a   Guzei, Ilia A ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Catalysis; Molecular oxygen; Oxidation; Palladium

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; MOLECULAR DYNAMICS; OXIDATION; OXYGEN; PALLADIUM COMPOUNDS;

AEROBIC OXIDATION REACTIONS; MOLECULAR OXYGEN;

REACTION KINETICS;

EID: 33745688109     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600532     Document Type: Article

References (47)

1. a) S. S. Stahl, Science 2005, 309, 1824;
2. b) S. S. Stahl, Angew. Chem. 2004, 116, 3480;
3. Angew. Chem. Int. Ed. 2004, 43, 3400;
4. c) M. S. Sigman, M. J. Schultz, Org. Biomol. Chem. 2004, 2, 2551;
5. d) B. M. Stoltz, Chem. Lett. 2004, 33, 362;
6. e) T. Nishimura, S. Uemura, Synlett 2004, 201;
7. f) R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774;
8. g) M. Toyota, M. Ihara, Synlett 2002, 1211.
9. a) W. R. Thiel, Angew. Chem. 1999, 111, 3349;
10. Angew. Chem. Int. Ed. 1999, 38, 3157;
11. b) S. S. Stahl, J. L. Thorman, R. C. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188;
12. c) M. M. Konnick, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 10212.
13. a) T. Hosokawa, S.-I. Murahashi, Acc. Chem. Res. 1990, 23, 49;
14. b) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750;
15. c) J. Muzart, J. P. Pete, J. Mol. Catal. 1982, 15, 373.
16. 2-peroxo-palladium(II) species, see: a) G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62;
17. Angew. Chem. Int. Ed. Engl. 1967, 6, 92;
18. b) C. J. Nyman, C. E. Wymore, G. Wilkinson, J. Chem. Soc. A 1968, 561;
19. c) S. Otsuka, A. Nakamura, Y. Tatsuno, J. Am. Chem. Soc. 1969, 91, 6994;
20. d) T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1977, 99, 2134;
21. e) T. Yoshida, K. Tatsumi, M. Matsumoto, K. Nakatsu, A. Nakamura, T. Fueno, S. Otsuka, Nouv. J. Chim. 1979, 3, 761;
22. f) W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, J. Chem. Soc. Dalton Trans. 2002, 3300;
23. g) G. Adjabeng, T. Brenstrum, C. S. Frampton, A. J. Robertson, J. Hillhouse, J. McNulty, A. Capretta, J. Org. Chem. 2004, 69, 5082;
24. h) M. Yamashita, K. Goto, T. Kawashima, J. Am. Chem. Soc. 2005, 127, 7294.
25. The first such example appeared recently: M. C. Denney, N. A. Smythe, K. L. Cetto, R. A. Kemp, K. I. Goldberg, J. Am. Chem. Soc. 2006, 128, 2508.
26. II-hydride bond, see: a) J. M. Keith, R. J. Nielsen, J. Oxgaard, W. A. Goddard, III, J. Am. Chem. Soc. 2005, 127, 13172;
27. b) T. Privalov, C. Linde, K. Zetterberg, C. Moberg, Organometallics 2005, 24, 885.
28. N. D. Clement, K. J. Cavell, C. Jones, C. J. Elsevier, Angew. Chem. 2004, 116, 1297;
29. Angew. Chem. Int. Ed. 2004, 43, 1277.
30. 2[15] with anisotropic displacement coefficients. All hydrogen atoms except H were included in the structure factor calculation at idealized positions and were allowed to ride on the neighboring atoms with relative isotropic displacement coefficients. The H istrotropic displacement coefficient was refined independently. CCDC-297730 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre by www.ccdc.cam.ac.uk/ data_request/cif.
31. III-hydride complexes, see: a) R. D. Gillard, B. T. Heaton, D. H. Vaughan, J. Chem. Soc. A 1970, 3126;
32. b) M. T. Atlay, M. Preece, G. Strukul, B. R. James, Can. J. Chem. 1983, 61, 1332.
33. a) J. F. Endicott, C.-L. Wong, T. Inoue, P. Natarajan, Inorg. Chem. 1979, 18, 450;
34. b) A. Bakac, J. Am. Chem. Soc. 1997, 119, 10726;
35. c) A. Bakac, J. Photochem. Photobiol. A 2000, 132, 87;
36. d) T. T. Wenzel, Stud. Surf. Sci. Catal. 1991, 66, 545;
37. e) D. D. Wick, K. I. Goldberg, J. Am. Chem. Soc. 1999, 121, 11 900.
38. 1H NMR spectroscopic studies reveal that resonances associated with the coordinated benzoate ligand in 4b broaden upon addition of sub-stoichiometric quantities of benzoic acid. This observation implies a fluxional process which involves an interaction between the free carboxylic acid and bound carboxylate ligand in 4b. The mechanistic implications of these observations are the subject of ongoing study.
39. II-hydride formation, see: a) C. Amatore, A. Jutand, G. Meyer, I. Carelli, I. Chiarotto, Eur. J. Inorg. Chem. 2000, 1855;
40. b) I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 13 178.
41. a) D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940;
42. Angew. Chem. Int. Ed. 2003, 42, 3810;
43. b) J. A. Mueller, C. P. Goller, M. S. Sigman, J. Am. Chem. Soc. 2004, 126, 9724;
44. c) M. J. Schultz, S. S. Hamilton, D. R. Jensen, M. S. Sigman, J. Org. Chem. 2005, 70, 3343.
45. M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. 2003, 115, 3636;
46. Angew. Chem. Int. Ed. 2003, 42, 3512.
47. Bruker-AXS (2000-2003) SADABS V.2.05, SAINT V.6.22, SHELXTL V.6.10 & SMART 5.622 Software Reference Manuals. Bruker-AXS, Madison, Wisconsin, USA.