The use of a planar chiral ligand to effect C-H activation with asymmetric induction at an iridium center. dramatically different C-H activation stereoselectivities for benzene and cyclohexane

Journal of the American Chemical Society

Volumn 120, Issue 13, 1998, Pages 3253-3254

  Andrew Mobley, T ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78649745802     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja974323f     Document Type: Letter

References (26)

1. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; p 1166.
2. (a) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 352.
3. (b) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 3929.
4. Hoyano, J. K.; McMaster, A. D.; Graham, W. A. G. J. Am. Chem. Soc. 1983, 105, 7190.
5. For reviews see: (a) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
6. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
7. (c) Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1989.
8. For rare examples of asymmetric induction in C-H activation chemistry, see: (a) Ma, Y.; Bergman, R. G. Organometallics 1994, 13, 2548; correction: Organometallics 1994, 13, 4648.
9. (b) Keyes, M. C.; Young, V. G.; Tolman, W. B. Organometallics 1996, 15, 4133.
10. (c) Miyafuji, A.; Katsuki, T. Synlett 1997, 836.
11. (a) Boehme, U.; Thiele, K.-H. J. Organomet. Chem. 1994, 472, 39.
12. (b) Avey, A.; Weakley, T. J. R.; Tyler, D. R. J. Am. Chem. Soc. 1993, 115, 7706.
13. (c) Flores, J. C.; Chien, J. C. W.; Rausch, M. D. Organometallics 1994, 13, 4140.
14. (d) Jutzi, P.; Heidemann, T.; Neumann, B.; Stammler, H. G. J. Organomet. Chem. 1994, 472, 27.
15. (e) Okuda, J.; Schattenmann, F. J.; Wocadlo, S.; Massa, W. Organometallics 1995, 14, 789.
16. (f) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623.
17. (a) Heinekey, D. M.; Hinkle, A. S.; Close, J. D. J. Am. Chem. Soc. 1996, 118, 5353.
18. (b) Heinekey, D. M.; Millar, J. M.; Koetzle, T. F.; Payne, N. G.; Zilm, K. W. J. Am. Chem. Soc. 1990, 112, 909.
19. Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1986, 108, 4814.
20. (a) Mobley, T. A.; Schade, C.; Bergman, R G. J. Am. Chem. Soc. 1995, 117, 7822.
21. (b) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
22. 3)Ir. Theoretical references:
23. (a) Song, J.; Hall, M. B. Organometallics 1993, 12, 3118.
24. (b) Margl, P.; Ziegler, T.; Blochl, P. E. J. Am. Chem. Soc. 1995, 117, 12625.
25. (c) Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 199.
26. 3 conversion of the Cp* ring to open a coordination site at the Ir center. For an analogous mechanism in a Tp*-substituted system, see: Bromberg, S. E.; Yang, H.; Asplund, M. C.; Lian, T.; McNamara, B. K.; Kotz, K. T.; Yeston, J. S.; Wilkens, M.; Frei, H.; Bergman, R. G.; Harris, C. B. Science 1997, 278, 260-263.