Insertion of dioxygen into a platinum-hydride bond to form a novel dialkylhydroperoxo Pt(IV) complex [4]

Journal of the American Chemical Society

Volumn 121, Issue 50, 1999, Pages 11900-11901

  Wick, Douglas D ^a   Goldberg, Karen I ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; HYDROPEROXIDE; PLATINUM COMPLEX;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; LETTER; OXIDATION; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0033596307     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992618i     Document Type: Letter

References (57)

1. (a) Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1989.
2. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
3. (c) Shilov, A. E.; Shul'pin, G. B. Chem, Rev. 1997, 97, 2879.
4. (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 5000.
5. (e) Waltz, K. M.; Hartwig, J. F. Science 1997, 277, 211.
6. (f) Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
7. (a) Ebner, J.; Riley, D. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional: London, 1995; p 205.
8. (b) Sen, A. Acc. Chem. Res. 1998, 31, 550.
9. (a) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560.
10. (b) Thorn, D. L.; Roe, D. C.; DeVries, N., to be published (personal communication, 1999).
11. (a) Wieghardt, K.; Köppen, M.; Swiridoff, W.; Weiss, J. J. Chem Soc., Dalton Trans. 1983, 1869.
12. (b) Rostovtsev, V. V.; Labinger, J. A.; Bercaw, J. E.; Lasseter, T. L.; Goldberg, K. I. Organometallics 1998, 17, 4530.
13. (c) Davies, M. S.; Hambley, T. W. Inorg. Chem. 1998, 37, 5408 and references therein.
14. (d) Prokopchuk, E. M.; Jenkins, H. A.; Puddephatt, R. J. Organometallics 1999, 18, 2861.
15. Wick, D. D.; Goldberg, K. I. J. Am. Chem. Soc. 1997, 119, 10235.
16. (a) Co(III) dimer with μ-OOH: Thewalt, U.; Marsh, R. J. Am. Chem. Soc. 1967, 89, 6364.
17. (b) Mo(VI) dimer with μ-OOH; Le Carpentier, J. M.; Mitschler. A.; Weiss, R. Acta Crystallogr., Sect. B 1972, 1288.
18. (c) Oxy hemerythrin; Holmes, M. A.; Le Trong, I.; Turley, S.; Sieker, L. C.; Stenkamp, R. E. J. Mol. Biol. 1991, 218, 583.
19. (d) Rh(III) in Rh(HI)-Ir(III): Carmona, D.; Lamata, M. P.; Ferrer, J.; Modrego, J.; Perales, M.; Lahoz, F. J.; Atencio, R.; Oro, L. A. J. Chem. Soc., Chem. Commun. 1994, 575.
20. (e) Cu(II) monomer: Wada, A.; Harata, M.; Hasegawa, K.; Jitsukawa, K.; Masuda, H.; Mukai, M.; Kitagawa, T.; Einaga, H. Angew. Chem., Int. Ed. 1998, 37, 798.
21. (a) Ho, R. Y. N.; Roelfes, G.; Feringa, B. L.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 264 and references therein.
22. (b) Root, D. E.; Mahroof-Tahir, M.; Karlin, K. D.; Solomon, E. I. Inorg. Chem. 1998, 37, 4838 and references therein.
23. (c) Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional: London, 1995.
24. (d) Thematic issue on Bioinorganic Enzymology. Chem. Rev. 1996, 96, 2237-3042.
25. O'Reilly, S. A.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1996, 118, 5684.
26. 12b See Supporting Information for experimental details and further characterization of 2.
27. Nakamoto, K. Infrared and Roman Spectra of Inorganic and Coordination Compounds; John Wiley & Sons: New York, 1978; p 298.
28. (a) Akita, M.; Ohta, K.; Takahashi, Y.; Hitachi, S.; Moro-oka, Y. Organometallics 1997, 16, 4121.
29. (b) Northcutt, T. O.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 5148.
30. (a) Roberts, H. L.; Symes, W. R. J. Chem Soc (A) 1968, 1450.
31. (b) Michelin, R. A.; Renzo, R.; Strukul, G. Inorg. Chim. Acta 1979, 37, L491.
32. (c) Strukul, G.; Renzo, R.; Michelin, R. A. Inorg. Chem. 1982, 21, 495.
33. (d) Atlay, M. T.; Preece, M.; Strukul, G.; James, B. R. Can. J. Chem. 1983, 61, 1332.
34. (e) Suzuki, H.; Matsuura, S.; Moro-oka, Y.; Ikawa, T. J. Organomet. Chem. 1985, 286, 247.
35. (f) Cenini, S.; Porta, F.; Pizzotti, M. J. Organomet. Chem. 1985, 296, 291.
36. (g) Miller, B.; Altman, J.; Beck, W. Inorg. Chim. Acta 1997, 264, 101.
37. (h) Akita, M.; Miyaji, T.; Hikichi, S.; Moro-oka, Y. J. Chem. Soc., Chem. Commun. 1998, 1005.
38. 3, Z = 4, RI = 0.0454 [I > 4σ(I)], GOF = 1.064. Selected bond distances (Å) for O1-O2, Pt1-O1. Pt1-CI, Pt1-C2, Pt1-N1, Pt1-N3, Pt1-N5: 1.481(5), 1.980(4), 2.070(5), 2.039(6), 2.037(4), 2.162-(4), 2.170(4). respectively. Selected bond angle (deg) for Pt1-O1-O2, 110.1(3).
39. 2 molecule are not shown.
40. A diagram of this hydrogen-bonding arrangement is provided in the Supporting Information.
41. 2O)H]: ref 12a.
42. 2O)H]: ref 12a.
43. 2: Johnston, L. E.; Page, J. A. Can. J. Chem. 1969, 47, 4241.
44. 2(OH)H]Cl: Gillard, R. D.; Heaton, B. T.; Vaughan, D. H. J. Chem. Soc. (A) 1970, 3126.
45. 2: ref 12d.
46. 4]: refod.
47. 2OH (3).
48. Light from an Oriel 200-W Hg/Xe (no. 6291) arc lamp was passed through a 345-nm long-pass quartz filter.
49. 2OH (3) and an unidentified Pt(IV) species with two methyl ligands and having a 2:1 pattern of pyrazolyl resonances.
50. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations, of Organic Compounds; Academic Press: New York, 1981; p 17.
51. (b) Walling, C. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J, F., Eds.; Blackie Academic & Professional: London, 1995; p 25.
52. +, calcd (found) 539.21438 (539.21413).
53. After ∼5 weeks, the reaction had proceeded to 92% conversion and 71% yield of 3. The remaining Pt-containing products were not identified.
54. (a) Pregaglia, G.; Morelli, D.; Conti, F.; Gregorio, G.; Ugo, R. Faraday Discuss,. Chem. Soc. 1968, 110.
55. (b) Karlin, K. D.; Ghosh, P.; Cruse, R. W.; Farooq, A.; Gultneh, Y.; Jacobson, R. R.; Blackburn, N. J.; Strange, R. W.; Zuhieta, J. J. Am. Chem. Soc. 1988, 110, 6769.
56. Hiatt, R.; Mill, T.; Mayo, F. R. J. Org. Chem. 1968, 33, 1416 and subsequent papers.
57. 2O has been used to convert a [Ru]-H to a [Ru]-OH complex: Kaplan. A. W.; Bergman, R. G. Organometallics 1998, 17, 5072.