Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation

Journal of the American Chemical Society

Volumn 131, Issue 21, 2009, Pages 7238-7239

  Koreeda, Tetsuro ^a   Kochi, Takuya ^a   Kakiuchi, Fumitoshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVES; BOND CLEAVAGES; C-C BOND FORMATION; CHEMICAL EQUATIONS; RUTHENIUM COMPLEXES; TRANSITION-METAL CENTERS;

CHEMICAL REACTIONS; OLEFINS; RUTHENIUM; RUTHENIUM COMPOUNDS;

CHEMICAL BONDS;

ALKENE DERIVATIVE; ANILINE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBON; NITROGEN; RUTHENIUM; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 67650566924     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902829p     Document Type: Article

References (33)

1. For catalytic functionalization via cleavage of unreactive C-H bonds, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev 2002, 102, 1731.
2. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
3. (c) Godula, K.; Sames, D. Science 2006, 312, 67.
4. (d) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
5. For C-C bonds, see: (e) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; pp 99-129.
6. (f) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
7. (g) Jun, C.-H.; Park, J.-W. Top. Organomet. Chem. 2007, 24, 117.
8. For C-F bonds, see: (h) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
9. (i) Ishii, Y.; Chatani, N.; Yorimitsu, S.; Murai, S. Chem. Lett. 1998, 157.
10. (j) Saeki, T.; Takashima, Y.; Tamao, K. Synlett 2005, 1771.
11. (k) Korn, T. J.; Schade, M. A.; Wirth, S.; Knochel, P. Org. Lett. 2006, 8, 725.
12. For C-O bonds, see: (l) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
13. (m) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706.
14. (n) Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428.
15. (o) Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516.
16. Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
17. For studies of catalytic reactions involving cleavage of activated aromatic C-N bonds, see: (a) Wenkert, E.; Han, A.-L.; Jenny, C.-J. J. Chem. Soc., Chem. Commun. 1988, 975.
18. (b) Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
19. (c) Saeki, T.; Son, E.-C.; Tamao, K. Org. Lett. 2004, 6, 617.
20. (d) Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622.
21. Bonnano, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
22. For cleavage of an aromatic C-N bond from a (N-silyl)arylamido molybdenum complex, see: Cameron, T. M.; Abboud, K. A.; Boncella, J. M. Chem. Commun. 2001, 1224.
23. Functionalization of aromatic C-N bonds using stoichiometric amounts of Pd complexes has been reported, but the mechanism is unclear. See: Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y.; Abe, M.; Taniguchi, H. J. Org. Chem. 1980, 45, 2359.
24. Cleavage of unactivated aliphatic C-N bonds on transition metals has been reported: (a) Takano, K.; Inagaki, A.; Akita, M. Chem. Lett. 2006, 35, 434.
25. (b) Burling, S.; Mahon, M. F.; Powell, R. E.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2006, 128, 13702.
26. (c) Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; de K. Lewis, A. K. Angew. Chem., Int. Ed. 2004, 43, 5824.
27. The (2-acylphenyl)amido ligand on 3 rapidly exchanges with free substrate 2 at 120°C in toluene. See the Supporting Information for datails.
28. (a) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
29. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. Also see footnote 9 in ref 1o.
30. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. Organometallics 1991, 10, 1875.
31. Ammonia was quantified by the indophenols-blue method: Weatherburn, M. W. Anal. Chem. 1967, 39, 971.
32. 2 group with another equivalent of 2a.
33. See the Supporting Information for details.