Rapid C-H bond activation by a monocopper(III)-hydroxide complex

Journal of the American Chemical Society

Volumn 133, Issue 44, 2011, Pages 17602-17605

  Donoghue, Patrick J ^a   Tehranchi, Jacqui ^a   Cramer, Christopher J ^a   Sarangi, Ritimukta ^b   Solomon, Edward I ^b,c   Tolman, William B ^a  

^a University of Minnesota   (United States)

^b SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CH-BOND ACTIVATION; CU COMPLEXES; DIHYDROANTHRACENE; H-ATOM ABSTRACTION; HIGH RATE; KINETIC ISOTOPE EFFECTS; KINETIC STUDY; ONE-ELECTRON OXIDATION; OXIDATION CATALYSIS; RATE LAWS; REACTIVE INTERMEDIATE; SECOND ORDERS;

ISOTOPES; REACTION RATES;

OXIDATION;

COPPER COMPLEX; HYDROGEN; HYDROXIDE; OXYGEN;

ARTICLE; BINDING KINETICS; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; OXIDATION; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

COPPER; CRYSTALLOGRAPHY, X-RAY; HYDROXIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 80455168001     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207882h     Document Type: Article

References (46)

1. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561
2. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605
3. Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379-3394
4. Que, L., Jr.; Tolman, W. B. Nature 2008, 455, 333-340
5. Woertink, J. S.; Smeets, P. J.; Groothaert, M. H.; Vance, M. A.; Sels, B. F.; Schoonheydt, R. A.; Solomon, E. I. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 18908-18913
6. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076
7. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045
8. Hatcher, L.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669-683
9. Itoh, S. Curr. Opin. Chem. Biol. 2006, 10, 115-122
10. For example, see: Itoh, S.; Fukuzumi, S. Acc. Chem. Res. 2007, 40, 592-600
11. Himes, R. A.; Karlin, K. D. Curr. Opin. Chem. Biol. 2009, 13, 119-131
12. Hong, S.; Gupta, A. K.; Tolman, W. B. Inorg. Chem. 2009, 48, 6323-6325 and references cited therein
13. Chen, P.; Solomon, E. I. J. Am. Chem. Soc. 2004, 126, 4991-5000
14. Evans, J. P.; Ahn, K.; Klinman, J. P. J. Biol. Chem. 2003, 278, 49691-49698
15. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Inorg. Chem. 2006, 45, 3034-3041
16. Crespo, A.; Marti, M. A.; Roitberg, A. E.; Amzel, L. M.; Estrin, D. A. J. Am. Chem. Soc. 2006, 128, 12817-12828
17. Schröder, D.; Holthausen, M. C.; Schwarz, H. J. Phys. Chem. B 2004, 108, 14407-14416
18. Dietl, N.; van der Linde, C.; Schlangen, M.; Beyer, M. K.; Schwarz, H. Angew. Chem., Int. Ed. 2011, 50, 4966-4969
19. Yoshihide, N.; Kimihiko, H.; Tetsuya, T. J. Chem. Phys. 2001, 114, 7935-7940
20. Decker, A.; Solomon, E. I. Curr. Opin. Chem. Biol. 2005, 9, 152-163
21. Gherman, B. F.; Heppner, D. E.; Tolman, W. B.; Cramer, C. J. J. Biol. Inorg. Chem. 2006, 11, 197-205
22. Huber, S. M.; Ertem, M. Z.; Aquilante, F.; Gagliardi, L.; Tolman, W. B.; Cramer, C. J. Chem.-Eur. J. 2009, 15, 4886-4895
23. Gherman, B. F.; Tolman, W. B.; Cramer, C. J. J. Comput. Chem. 2006, 27, 1950-1961
24. Protonation of a species with core F to yield a compound with core G has been postulated: Reinaud, O.; Capdevielle, P.; Maumy, M. J. Chem. Soc., Chem. Commun. 1990, 566-568
25. Some reported Cu-OH bond distances in terminal moncopper-hydroxide complexes: (1.878(2) Å) Berreau, L. M.; Mahapatra, S.; Halfen, J. A.; Young, V. G., Jr.; Tolman, W. B. Inorg. Chem. 1996, 35, 6339-6342
26. (1.875(2) Å)
27. Lee, S. C.; Holm, R. H. J. Am. Chem. Soc. 1993, 115, 11789-1198
28. Parkin, G. Chem. Rev. 1993, 93, 887-911
29. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2 nd ed.; Wiley & Sons: New York, 2004; p 291.
30. DuBois, J. L.; Mukherjee, P.; Stack, T. D. P.; Hedman, B.; Solomon, E. I.; Hodgson, K. O. J. Am. Chem. Soc. 2000, 122, 5775-5787
31. Shi, S.; Wang, Y.; Xu, A.; Wang, H.; Zhu, D.; Roy, S. B.; Jackson, T. A.; Busch, D. H.; Yin, G. Angew. Chem., Int. Ed. 2011, 50, 7321-7324 and references cited therein
32. Lockwood, M. A.; Blubaugh, T. J.; Collier, A. M.; Lovell, S.; Mayer, J. M. Angew. Chem., Int. Ed. 1999, 38, 225-227
33. Roth, J. P.; Mayer, J. M. Inorg. Chem. 1999, 38, 2760-2761
34. Goldsmith, C. R.; Stack, T. D. P. Inorg. Chem. 2006, 45, 6048-6055
35. Parsell, T.; Yang, M.; Borovik, A. J. Am. Chem. Soc. 2009, 131, 2762-2763
36. Gardner, K. A.; Kuehnert, L. L.; Mayer, J. M. Inorg. Chem. 1997, 36, 2069-2078
37. Goldsmith, C. R.; Cole, A. P.; Stack, T. D. P. J. Am. Chem. Soc. 2005, 127, 9904-9912
38. Xue, G.; De Hont, R.; Münck, E.; Que, L., Jr. Nat. Chem. 2010, 2, 400-405
39. Rittle, J.; Green, M. T. Science 2010, 330, 933-937
40. Itoh, S. Curr. Opin. Chem. Biol. 2006, 10, 115-122
41. Green, M. T. Curr. Opin. Chem. Biol. 2009, 13, 84-88
42. Prokop, K. A.; de Visser, S. P.; Goldberg, D. P. Angew. Chem., Int. Ed. 2010, 49, 5091-5095
43. Borovik, A. S. Chem. Soc. Rev. 2011, 40, 1870-1874
44. Nieto, I.; Ding, F.; Bontchev, R. P.; Wang, H.; Smith, J. M. J. Am. Chem. Soc. 2008, 130, 2716-2717
45. Reitz, J. B.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 11467-11478
46. Mayer, J. M. Acc. Chem. Res. 2011, 44, 36-46