Characterization of peroxo and hydroperoxo intermediates in the aerobic oxidation of N-heterocyclic-carbene-coordinated palladium(0)

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10212-10213

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

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; HETEROCYCLIC NITRO COMPOUND; HYDROGEN PEROXIDE; HYDROPEROXIDE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COMPLEX FORMATION; DISSOCIATION; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 4143086010     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046884u     Document Type: Article

References (31)

1. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
2. (b) Nishimura, T.; Uemura, S. Synlett 2004, 201-216.
3. (c) Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
4. (d) Sigman, M. S.; Jensen, D. R.; Rajaram, S. Curr. Opin. Drug Discovery Dev. 2002, 5, 860-869.
5. (e) Toyota, M.; Ihara, M. Synlett 2002, 1211-1222.
6. (f) Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781.
7. (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
8. (b) Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; Kluwer: Boston, 1980.
9. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188-7189.
10. For examples of NHC-coordinated palladium complexes used in aerobic oxidation catalysis, see: (a) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810-3813.
11. (b) Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63-65.
12. (c) Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 12996-12997.
13. Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A., J. Organomet. Chem. 2000, 595, 186-190.
14. Full characterization data are provided in the Supporting Information.
15. 2 dissociation included sparging a toluene solution of 3 with nitrogen gas, attempted sublimation of 3 (which led to decomposition), and stirring a solution of 3 in mesitylene under full vacuum at 40 °C.
16. The role of spin-state effects on the kinetics of transition-metal reactions continues to be actively debated. See, for example: (a) Carreón-Macedo, J.-L.; Harvey, J. N. J. Am. Chem. Soc. 2004, 126, 5789-5797.
17. (b) Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745-11748.
18. (c) Schrock, R. R.; Shih, K.-Y.; Dobbs, D. A.; Davis, W. M. J. Am. Chem. Soc. 1995, 117, 6609-6610.
19. Computational studies are being conducted to probe spin-state effects on this reaction pathway: Morales, C. M.; Stahl, S. S.; Landis, C. R. Unpublished results.
20. Pd-OOH complexes prepared from hydrogen peroxide have been reported: (a) Strukul, G.; Ros, R.; Michelin, R. A. Inorg. Chem. 1982, 21,495-500.
21. (b) Miyaji, T.; Kujime, M.; Hikichi, S.; Moro-oka, Y.; Akita, M. Inorg. Chem. 2002, 41, 5286-5295.
22. (a) Eisenberg, G. M. Ind. Eng. Chem. Anal. Ed. 1943, 15, 327-328.
23. (b) Wemer, W. U.S. Patent 4, 908, 323, 1990.
24. For details, see Supporting Information. Partial disproportionation of hydrogen peroxide may occur under the reaction conditions: Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766-767.
25. (a) Wilke, G.; Schott, H.; Heimbach, P. Angew. Chem., Int. Ed. Engl. 1967, 6, 92-93.
26. (b) Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1977, 99, 2134-2140.
27. (c) Yoshida, T.; Tatsumi, K.; Matsumoto, M.; Nakatsu, K.; Nakamura, A.; Fueno, T.; Otsuka, S. Nouv. J. Chim. 1979, 3, 761-774.
28. Jacobi, B. G.; Laitar, D. S.; Pu, L.; Wargocki, M. F.; DiPasquale, A. G.; Fortner, K. C.; Schuck, S. M.; Brown, S. N. Inorg. Chem. 2002, 41, 4815-4823.
29. (a) Nishimura, T.; Kakiuchi, N.; Onoue, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 1915-1918.
30. (b) Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49-54.
31. (c) Igersheim, F.; Mimoun, H. Nouv. J. Chim. 1980, 4, 711-713.