Acceleration of nucleophilic CH activation by strongly basic solvents

Journal of the American Chemical Society

Volumn 132, Issue 36, 2010, Pages 12542-12545

  Hashiguchi, Brian G ^a   Young, Kenneth J H ^b   Yousufuddin, Muhammed ^c   Goddard, William A ^d   Periana, Roy A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^c UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^d CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BASIC SOLVENTS; C-H ACTIVATION; H/D EXCHANGE; PINCER LIGANDS; SOLVENT BASICITIES;

HYDROCARBONS;

SOLVENTS;

HYDROCARBON; PYRIDINE DERIVATIVE; RUTHENIUM COMPLEX; SOLVENT;

ALKALINITY; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; SOLVENTS;

EID: 77956421310     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102518m     Document Type: Article

References (38)

1. We define the CH activation reaction as a coordination reaction that proceeds without the involvement of free radicals, carbocations, or carbanions to generate discrete M-R intermediates. Shilov, A. E. and Shul'pin, G. B. Chem. Rev. 1997, 97, 2879
2. Arndtsen, B. A., Bergman, R. G., Mobley, T. A., and Peterson, T. H. Acc. Chem. Res. 1995, 28, 154 and citations therein
3. Periana, R. A., Bhalla, G., Tenn, W. J., III, Young, K. J. H., Liu, X. Y., Mironov, O., Jones, C., and Ziatdinov, V. R. J. Mol. Catal. A: Chem. 2004, 220, 7 and citations therein
4. Conley, B. L., Tenn, W. J., III, Young, K. J. H., Ganesh, S. K., Meier, S. K., Ziatdinov, V. R., Mironov, O., Oxgaard, J., Gonzales, J., Goddard, W. A., III, and Periana, R. A. J. Mol. Catal. A: Chem. 2006, 251, 8
5. Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083
6. Lersch, M. and Tilset, M. Chem. Rev. 2005, 105, 2471
7. Ess, D. H., Nielsen, R. J., Goddard, W. A., III, and Periana, R. A. J. Am. Chem. Soc. 2009, 131, 11686
8. Kua, J., Xu, X., Periana, R. A., and Goddard, W. A., III. Organometallics 2002, 21, 511
9. Ahlquist, M., Periana, R. A., and Goddard, W. A., III. Chem Commun. 2009, 2373
10. Tenn, W. J., Young, K. J. H., Oxgaard, J., Nielsen, R. J., Goddard, W. A., III, and Periana, R. A. Organometallics 2006, 25, 5173
11. Tenn, W. J., III, Young, K. J. H., Bhalla, G., Oxgaard, J., Goddard, W. A. III, and Periana, R. A. J. Am. Chem. Soc. 2005, 127, 14172
12. Young, K. J. H., Oxgaard, J., Ess, D. H., Meier, S. K., Stewart, T., Goddard, W. A., III, and Periana, R. A. Chem. Commun. 2009, 3270
13. Foley, N. A., Lee, J. P., Ke, Z., Gunnoe, T. B., and Cundari, T. R. Acc. Chem. Res. 2009, 42, 585 and citations therein
14. Meier, S. K., Young, K. J. H., Ess, D. H., Tenn, W. J., III, Oxgaard, J., Goddard, W. A., III, and Periana, R. A. Organometallics 2009, 28, 5293
15. Oxgaard, J., Muller, R. P., Goddard, W. A., III, and Periana, R. A. J. Am. Chem. Soc. 2004, 126, 352
16. Lail, M., Bell, C. M., Conner, D., Cundari, T. R., Gunnoe, T. B., and Petersen, J. L. Organometallics 2004, 23, 5007
17. Conley, B. L., Ganesh, S. K., Gonzales, J. M., Tenn, W. J., III, Young, K. J. H., Oxgaard, J., Goddard, W. A., III, and Periana, R. A. J. Am. Chem. Soc. 2006, 128, 9018
18. Gonzales, J. M., Distasio, R., Jr., Periana, R. A., Goddard, W. A., III, and Oxgaard, J. J. Am. Chem. Soc. 2007, 129, 15794
19. Conley, B. L., Ganesh, S. K., Gonzales, J. M., Ess, D. H., Nielsen, R. J., Ziatdinov, V. R., Oxgaard, J., Goddard, W. A., III, and Periana, R. A. Angew. Chem., Int. Ed. 2008, 47, 7849
20. Himeda, Y., Onozawa-Komatsuzaki, N., Sugihara, H., and Kasuga, K. Organometallics 2007, 26, 702
21. Irreversible deprotonation of all protics ligands will prevent further modulation of the catalysis by ligand deprotonation at higher basicities.
22. Fulton, J. R., Holland, A. W., Fox, D. J., and Bergman, R. G. Acc. Chem. Res. 2002, 35, 44 and citations therein
23. Basolo, F. Pure Appl. Chem. 1968, 17, 37
24. Jackson, W. G. Inorg. React. Mech. 2002, 4, 1
25. See SI for conjugate mechanism.
26. Stupka, G., Gremaud, L., Bernardinelli, G., and Williams, A. F. Dalton Trans. 2004, 40, 7-412 and citations therein
27. Voss, M. E., Beer, C. M., Mitchell, S. A., Blomgren, P. A., and Zhichkin, P. E. Tetrahedron 2008, 64, 645
28. Based upon X-ray analysis, see SI for details.
29. 2H NMR spectroscopy showed deuterium incorporation into IA.
30. Klei, S. R., Golden, J. T., Tilley, T. D., and Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 2092
31. Prechtl, M. H. G., Hölscher, M., Ben-David, Y., Theyseen, N., Loschen, R., Milstein, D., and Leitner, W. Angew. Chem., Int. Ed. 2007, 119, 2319 and citations therein
32. Meier, S. K., Young, K. J. H., Ess, D. H., Tenn, W. J., III, Oxgaard, J., Goddard, W. A., III, and Periana, R. A. Organometallics 2009, 28, 5293 and citations therein
33. Feng, Y., Jiang, B., Boyle, P. A., and Ison, E. A. Organometallics 2010, 29, 2857
34. -1.
35. Fulton, J. R., Bouwkamp, M. W., and Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 8799-8800
36. Fulton, J. R., Sklenak, S., Bouwkamp, M. W., and Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 4722
37. a of free IPI is 14, but that of the coordinated IPI will depend on the other species coordination to Ru.
38. Rochester, C. H. Q. Rev. Chem. Soc. 1966, 20, 511