A catalytic cycle for oxidation of tert-butyl methyl ether by a double C-H activation-group transfer process

Journal of the American Chemical Society

Volumn 130, Issue 49, 2008, Pages 16476-16477

  Whited, Matthew T ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; CARBON; HYDROGEN; INDIUM; LIGAND; METAL COMPLEX; NITROGEN; TERT BUTYL METHYL ETHER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 57549086597     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8071385     Document Type: Article

References (35)

1. For leading references, see: (a) Bergman, R. G. Nature 2007, 446, 391.
2. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
3. (c) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
4. (d) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
5. (e) Activation and Functionalization of C-H Bonds; Goldberg, K. I., Goldman, A. S., Eds.; ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004.
6. (f) Periana, R. A.; Bhalla, G.; Tenn, W. J.; Young, K. J. H.; Liu, X. Y.; Mironov, O.; Jones, C. J.; Ziatdinov, V. R. J. Mol. Catal. A: Chem. 2004, 220, 7.
7. Stoichiometric generation of iridium carbenes by double C-H activation of ethers: (a) Boutry, O.; Gutiérrez, E.; Monge, A.; Nicasio, M. C.; ; Pérez, P. J.; Carmona, E. J. Am. Chem. Soc. 1992, 114, 7288.
8. (b) Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517.
9. (c) Carmona, E.; Paneque, M.; Santos, L. L.; Salazar, V. Coord. Chem. Rev. 2005, 249, 1729.
10. (a) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
11. (b) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
12. (c) Doyle, M. P. Chem. Rev. 1986, 86, 919.
13. (d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
14. (a) Fan, L.; Foxman, B. M.; Ozerov, O. V. Organometallics 2004, 23, 326.
15. (b) Ozerov, O. V.; Guo, C.; Papkov, V. A.; Foxman, B. M. J. Am. Chem. Soc. 2004, 126, 4792.
16. (a) Whited, M. T.; Grubbs, R. H. J. Am. Chem. Soc. 2008, 130, 5874.
17. (b) Romero, P. E.; Whited, M. T.; Grubbs, R. H. Organometallics 2008, 27, 3422.
18. Whited, M. T.; Grubbs, R. H. Organometallics, in press.
19. A related but distinct tandem alkane dehydrogenation-olefin metathesis process has recently been reported for catalytic C-H functionalization via metal carbene intermediates: Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinski, W.; Brookhart, M. Science 2006, 312, 257.
20. (a) Matsunaga, P. T.; Hess, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 1994, 116, 3665.
21. (b) Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075.
22. Interestingly, Hillhouse reports that pyridine N-oxide does not perform this transformation (ref 8b). We note the same behavior in our system, probably due to the poor electrophilicity of the reagent.
23. 2 has been reported: Gatard, S.; Guo, C.; Foxman, B. M.; Ozerov, O. V. Organometallics 2007, 26, 6066.
24. (a) Fischer, H.; Zeuner, S. J. Organomet. Chem. 1985, 286, 201.
25. (b) Hu, X.; Meyer, K. J. Am. Chem. Soc. 2004, 126, 16322.
26. (c) Harrold, N. D.; Waterman, R.; Hillhouse, G. L. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL; American Chemical Society: Washington, DC, 2007; INOR 682.
27. Related reactivity of Fischer carbenes with diazoalkanes: (a) Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1972, 94, 6543.
28. (b) Casey, C. P.; Bertz, S. H.; Burkhardt, T. J. Tetrahedron Lett. 1973, 1421.
29. For leading references regarding reactivity of organic azides, see: Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234.
30. (a) Collman, J. P.; Kang, J. W. J. Am. Chem. Soc. 1966, 88, 3459.
31. (b) Collman, J. P.; Kubota, M.; Sun, J.-Y.; Vastine, F. D. J. Am. Chem. Soc. 1967, 89, 169.
32. (c) Collman, J. P.; Kubota, M.; Vastine, F. D.; Sun, J. Y.; Kang, J. W. J. Am. Chem. Soc. 1968, 90, 5430.
33. MacKay, B. A.; Fryzuk, M. D. Chem. Rev. 2004, 104, 385.
34. (a) Göttker-Schnettman, I.; White, P. S.; Brookhart, M. Organometallics 2004, 23, 1766.
35. (b) Ghosh, R.; Kanzelberger, M.; Emge, T. J.; Hall, G. S.; Goldman, A. S. Organometallics 2006, 25, 5668.