Stoichiometric oxy functionalization and CH activation studies of cyclometalated iridium(III) 6-phenyl-2,2′-bipyridine hydrocarbyl complexes

Organometallics

Volumn 26, Issue 9, 2007, Pages 2137-2140

  Young, Kenneth J H ^a   Mironov, Oleg A ^a   Periana, Roy A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CH ACTIVATION; HYDROCARBYL COMPLEXES; PROTIC-STABLE; TRIFLUOROACETIC ACID;

ACETIC ACID; ACTIVATION ENERGY; BENZENE; OXIDANTS; STOICHIOMETRY; THERMAL EFFECTS;

IRIDIUM COMPOUNDS;

EID: 34248339224     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0611002     Document Type: Article

References (32)

1. We define the CH activation reaction as a reaction between the reactive species "M" that proceeds without the involvement of free radicals, carbocations, or carbanions to generate discrete M-R intermediates, (a) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154 and references therein.
2. (b) Periana, R. A.; Bhalla, G.; Tenn, W. J., III; Young, K. J. H.; Liu, X. Y.; Mironov, O.; Jones, C. J.; Ziatdinov, V. R. J. Mol. Catal. A: Chem. 2004, 220, 7 and references therein.
3. Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083 and references therein.
4. (a) Klei, S. R.; Tan, K. L.; Golden, J. T.; Yung, C. M.; Thalji, R. K.; Ahrendt, K. A.; Ellman, J. A.; Tilley, T. D.; Bergman, R. G. In Activation and Functionalization of C-H Bonds; Goldberg, K. I., Goldman, A. S. Ed., ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004; 46.
5. (b) Bergman, R. G. Science 1984, 223, 902.
6. (a) Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560.
7. (b) Shilov, A. E.; Shul'pin, G. B. Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes; Kluwer Academic: Dordrecht, The Netherlands, 2000; p 560.
8. (c) Periana, R. A.; Mironov, O.; Taube, D.; Bhalla, G.; Jones, C. J. Science 2003, 301, 814.
9. (d) Muehlhofer, M.; Strassner, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1745.
10. 3 complexes forming esters: (a) Bernard, K. A.; Atwood, J. D. Organometallics 1987, 6, 1133.
11. (b) Bernard, K. A.; Atwood, J. D. Organometallics 1988, 7, 235.
12. (c) Bernard, K. A.; Atwood, J. D. Organometallics 1989, 8, 795.
13. (a) Thompson, J. S.; Randall, S. L.; Atwood, J. D. Organometallics 1991, 10, 3906.
14. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
15. 3: Thompson, J. S.; Atwood, J. D. Organometallics 1991, 10, 3525.
16. I - pyrrole through an Ir(III) intermediate: Driver, M. S.; Hartwig, J. F. Organometallics 1998, 17, 1134.
17. 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 and references therein.
18. Conley, B. L.; Ganesh, S. K.; Gonzales, J. M.; Tenn, W. J., III; Young, K. J. H.; Oxgaard, J.; Goddard, W. A., III: Periana, R. A. J. Am. Chem. Soc. 2006, 128, 9018.
19. Stable to dry air. It slowly reacts with moisture.
20. (a) Novak, F.; Speiser, B.; Mohammad, H. A. Y.; Mayer, H. A. Electrochim. Acta 2004, 49, 3481.
21. (b) Castillo-Blum, S. E.; Richens, D. T.; Sykes, A. G. Inorg. Chem. 1989, 28, 954.
22. (c) Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, A.; Pinzino, C.; Uccello-Barretta, G.; Zanello, P. Organometallics 1995, 14, 3275.
23. A reviewer has suggested another mechanism that involves nucleophilic attack of acetate (or trifluoroacatate) at the Ir-bound Me group, which might also explain the lack of reactivity of the phenyl complex.
24. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114.
25. (a) Hamamoto, H.; Hata, K.; Nambu, H.; Shiozaki, Y.; Tohma, H.; Kita, Y. Tetrahedron Lett. 2004, 45, 2293.
26. (b) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244 and references therein.
27. (c) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684.
28. An example of alkane oxidation through a cation radical mechanism: In, J.-H.; Park, S.-E.; Song, R.; Nam, W. Inorg. Chim. Acta 2003, 343, 373.
29. Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35.
30. (a) Dick, A.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
31. (b) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
32. (c) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.