Facile and regioselective C-H bond activation of aromatic substrates by an fe(II) complex involving a spin-forbidden pathway

Organometallics

Volumn 32, Issue 6, 2013, Pages 1797-1806

  Kalman, Steven E ^a   Petit, Alban ^b   Gunnoe, T Brent ^a   Ess, Daniel H ^b   Cundari, Thomas R ^c   Sabat, Michal ^d  

^a UNIVERSITY OF VIRGINIA   (United States)

^b Brigham Young University   (United States)

^c UNIVERSITY OF NORTH TEXAS   (United States)

^d University of Virginia   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SUBSTRATES; BOND METATHESIS; C-H ACTIVATION; C-H BOND CLEAVAGE; CH-BOND ACTIVATION; INTER-SYSTEM CROSSINGS; PENTAMETHYLCYCLOPENTADIENYL; REGIO-SELECTIVE;

ACTIVATION ANALYSIS; IRON COMPOUNDS; REGIOSELECTIVITY; THIOPHENE;

COORDINATION REACTIONS;

EID: 84875467050     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om301219t     Document Type: Article

References (45)

1. Goj, L. A.; Gunnoe, T. B. Curr. Org. Chem. 2005, 9, 671-685
2. Goldberg, K. I.; Goldman, A. S. Activation and Functionalization of C-H Bonds; American Chemical Society: Washington, D.C., 2004; Vol. 885.
3. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236-10254
4. Gunay, A.; Theopold, K. H. Chem. Rev. 2010, 110, 1060-1081
5. Wang, D.; Farquhar, E. R.; Stubna, A.; Munck, E.; Que, L. Nat. Chem. 2009, 1, 145-150
6. Gamez, P.; Aubel, P. G.; Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 30, 376-385
7. Goldsmith, C. R.; Cole, A. P.; Stack, T. D. P. J. Am. Chem. Soc. 2005, 127, 9904-9912
8. Gephart, R. T.; Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H. Angew. Chem., Int. Ed. 2012, 51, 6488-6492
9. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450
10. Wiese, S.; McAfee, J. L.; Pahls, D. R.; McMullin, C. L.; Cundari, T. R.; Warren, T. H. J. Am. Chem. Soc. 2012, 134, 10114-10121
11. Bullock, R. M. Catalysis without Precious Metals; Wiley-VCH Verlag & Co.: Weinheim, Germany, 2010.
12. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 5 th ed.; John Wiley and Sons: New York, 2009.
13. Ohki, Y.; Hatanaka, T.; Tatsumi, K. J. Am. Chem. Soc. 2008, 130, 17174-17186
14. Ittel, S. D.; Tolman, C. A.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1978, 100, 7577-7585
15. Tolman, C. A.; Ittel, S. D.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1978, 100, 4080-4089
16. Baker, M. V.; Field, L. D. J. Am. Chem. Soc. 1986, 108, 7433-7434
17. Hatanaka, T.; Ohki, Y.; Tatsumi, K. Chem.-Asian J. 2010, 5, 1657-1666
18. Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 16170-16171
19. Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047-5048
20. Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507
21. Foley, N. A.; Gunnoe, T. B.; Cundari, T. R.; Boyle, P. D.; Petersen, J. L. Angew. Chem., Int. Ed. 2007, 47, 726-730
22. Foley, N. A.; Lee, J. P.; Ke, Z.; Gunnoe, T. B.; Cundari, T. R. Acc. Chem. Res. 2009, 42, 585-597
23. Foley, N. A.; Lail, M.; Lee, J. P.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2007, 129, 6765-6781
24. Joslin, E. E.; McMullin, C. L.; Gunnoe, T. B.; Cundari, T. R.; Sabat, M.; Myers, W. H. Organometallics 2012, 31, 6851-6860
25. Morello, G. Ph.D. Thesis. Modeling transition metal chemistry for catalytic functionalization of molecules. University of North Texas, 2011.
26. Tellers, D. M.; Skoog, S. J.; Bergman, R. G.; Gunnoe, T. B.; Harman, W. D. Organometallics 2000, 19, 2428-2432
27. Diaz, C.; Cabezas, N.; Mendizabal, F. Bol. Soc. Chil. Quim. 2002, 47, 213-220
28. Jacobson, S. E.; Wojcicki, A. J. Am. Chem. Soc. 1973, 95, 6962-6970
29. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
30. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
31. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 4538-4543
32. Poli, R. Chem. Rev. 1996, 96, 2135-2204
33. Poli, R.; Harvey, J. N. Chem. Soc. Rev. 2003, 32, 1-8
34. Schroder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139-145
35. Lam, W. H.; Jia, G.; Lin, Z.; Lau, C. P.; Eisenstein, O. Chem.-Eur. J. 2003, 9, 2775-2782
36. Brooks, B. C.; Gunnoe, T. B.; Harman, W. D. Coord. Chem. Rev. 2000, 206-207, 3-61
37. Petit, A.; Flygare, J.; Miller, A. T.; Winkel, G.; Ess, D. H. Org. Lett. 2012, 14, 3680-3683
38. Pittard, K. A.; Lee, J. P.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2004, 23, 5514-5523
39. Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749-823
40. Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 91-100
41. Clot, E.; Megret, C.; Eisenstein, O.; Perutz, R. N. J. Am. Chem. Soc. 2006, 128, 8350-8357
42. Yasuda, S.; Yorimitsu, H.; Oshima, K. Organometallics 2010, 29, 273-274
43. Frisch, M. J., Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
44. Harvey, J. N.; Aschi, M.; Schwarz, H.; Koch, W. Theor. Chem. Acc. 1998, 99, 95-99
45. Harvey, J. N.; Aschi, M. Phys. Chem. Chem. Phys. 1999, 1, 5555-5563