Insertion of molecular oxygen into a palladium(II) hydride bond

Journal of the American Chemical Society

Volumn 128, Issue 8, 2006, Pages 2508-2509

  Denney, Melanie C ^a   Smythe, Nicole A ^a   Cetto, Kara L ^a   Kemp, Richard A ^a   Goldberg, Karen I ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN; PALLADIUM; PALLADIUM COMPLEX;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; OXIDATION;

EID: 33644638340     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0562292     Document Type: Article

References (27)

1. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400 and references therein.
2. (b) Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212.
3. (c) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
4. (a) Takehira, K.; Hayakawa, T.; Orita, H.; Shimizu, M. Stud. Org. Chem. (Amsterdam) 1988, 33, 307.
5. (b) Takehira, K.; Hayakawa, T.; Orita, H.; Shimizu, M. J. Mol. Catal. 1989, 53, 15.
6. (c) Hosokawa, T.; Murahashi, S. Acc. Chem. Res. 1990, 23, 49.
7. (d) Hosokawa, T.; Nakahira, T.; Takano, M.; Murahashi, S. J. Mol. Catal. 1992, 74, 489.
8. (e) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
9. (f) Nishimura, T.; Kakiuchi, N.; Onoue, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 1915.
10. (g) Keith, J. M.; Nielsen, R. J.; Oxgaard, J.; Goddard, W. A, III. J. Am. Chem. Soc. 2005, 127, 13172.
11. (a) Wenzel, T. T. Stud. Surf. Sci. Catal. 1991, 66, 545.
12. (b) Wick, D. D.; Goldberg, K. I. J. Am. Chem. Soc. 1999, 121, 11900.
13. (c) Thyagarajan, S.; Incarvito, C. D.; Rheingold, A. L.; Theopold, K. H. Chem. Commun. 2001, 2198.
14. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020.
15. Cámpora, J.; Palma, P.; Del Río, D.; Álvarez, E. Organometallics 2004, 23, 1652.
16. Characterization data for 2 and 3 are in the Supporting Information.
17. (a) Rostovtsev, V. V.; Henling, L. M.; Labinger, J. A.; Bercaw, J. E. Inorg. Chem. 2002, 41, 3608.
18. (b) Miyaji, T.; Kujime, M.; Hikichi, S.; Morooka, Y.; Akita, M. Inorg. Chem. 2002, 41, 5286 and references therein.
19. (c) Ahijado, M.; Braun, T.; Noveski, D.; Kocher, N.; Neumann, B.; Stalke, D.; Stammler, H.-G. Angew. Chem., Int. Ed. 2005, 44, 6947.
20. Farrugia, L. R. J. Appl. Crystallogr. 1997, 30, 565.
21. 2 (Battino, R. Oxygen and Ozone; Solubility Data Ser.; Pergamon Press: Oxford, 1981; Vol. 7).
22. Atkins, P.; de Paula, J. Physical Chemistry, 7th ed.; W. H. Freeman & Company; New York, 2002; p 888.
23. Endicott, J. F.; Wong, C.-L.; Inoue, T.; Natarajan, P. Inorg. Chem. 1979, 18, 450 and subsequent references.
24. Several common radical inhibitors have been reported to react with palladium hydride species (Albénia, A. C.; Espinet, P.; López-Fernández, R.; Sen, A. J. Am. Chem. Soc. 2002, 124, 11278). Galvinoxyl was found to react directly with 1. TEMPO and BHT did not react with 1.
25. (a) Pregalia, G.; Morelli, D.; Conti, F.; Gregorio, G.; Ugo, R. Faraday-Discuss. Chem. Soc. 1968, 110.
26. (b) Karlin, K. D.; Ghosh, P.; Cruse, R. W.; Farooq, A.; Gultneh, Y.; Jacobson, R. R.; Blackburn, N. J.; Strange, R. W.; Zubieta, J. J. Am. Chem. Soc. 1988, 110, 6769.
27. Hiatt, R.; Mill, T.; Mayo, F. R. J. Org. Chem. 1968, 33, 1416 and subsequent papers.