Oxidative C-H activation/C-C bond forming reactions: Synthetic scope and mechanistic insights

Journal of the American Chemical Society

Volumn 127, Issue 20, 2005, Pages 7330-7331

  Kalyani, Dipannita ^a   Deprez, Nicholas R ^a   Desai, Lopa V ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYL 3 METHYLPYRIDINE; 2 PYRROLIDONE DERIVATIVE; BENZENE; DICHLOROMETHANE; HETEROCYCLIC COMPOUND; IODINE DERIVATIVE; ORGANIC SOLVENT; OXAZOLIDINONE DERIVATIVE; OXIDIZING AGENT; PALLADIUM; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 19744365933     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051402f     Document Type: Article

References (30)

1. Metal-Catalyzed Cross-Coupling Reactions; Dieterich, F., Stang, P. J., Eds; Wiley-VCH: New York, 1998.
2. For recent examples of Pd(0)/(II)-catalyzed C-H activation/arylation of activated arenes/heterocycles, see: (a) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
3. (b) Park, C.-H.; Ryabova, V.; Scregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
4. (c) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301.
5. For recent examples of Pd(0)/Pd(II)-catalyzed C-H activation/arylation of unactivated arenes/alkanes, see: (a) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
6. (b) Wakui, H.; Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2004, 126, 8658 and references therein.
7. (c) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
8. (d) Sezen, B.; Franz, R.; Sames, D. J. Am. Chem. Soc. 2002, 124, 13372.
9. For related Ru-catalyzed imine and pyridine-directed C-H activation/arylation reactions, see: (a) Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783.
10. (b) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
11. For other examples of C-H activation/C-C bond forming reactions, see: (a) Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156.
12. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
13. (c) Davies, H. M. L.; Jin, Q. J. Am. Chem. Soc. 2004, 126, 10862.
14. (d) Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguschi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004. 126, 14342.
15. (e) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
16. (f) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
17. (a) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
18. (b) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
19. Canty, A. J.; Patel, J.; Rodemann, T.; Ryan, J. H.; Skelton, B. W.; White, A. H. Organometallics 2004, 23, 3466.
20. For the use of iodine(III) arylating agents in Pd(II)/(0) C-C bond forming reactions, see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
21. Ar bond forming reactions in which evidence supports the intermediacy of Pd(IV), see: (a) Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78 and references therein.
22. (b) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
23. For a related stoichiometric reaction, see: (c) Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
24. Palladacycle-catalyzed Heck reactions were originally proposed to proceed via a Pd(II)/(IV) cycle; however, more recent experiments (e.g., Hg poisoning studies) suggest that most of these reactions are actually catalyzed by Pd(0) nanoparticles. Eberhard, M. R.; Wang, Z. Org. Lett. 2004, 6, 2125 and references therein.
25. For some potential exceptions, see: van der Boom, M.; Milstein, D. Chem. Rev. 2003, 103, 1759.
26. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1997, 70, 3117.
27. Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R., III. J. Am. Chem. Soc. 2003, 125, 7792.
28. Snieckus, V. Chem. Rev. 1990, 90, 879.
29. Similar steric effects have been observed in Cr-catalyzed aldehyde arylation. Chen, D.; Ochiai, M. J. Org. Chem. 1999, 64, 6804.
30. 4 produces 1a in quantitative yield in the presence of 2.5 equiv of a free arylpyridine substrate, such as 3. Without the addition of 3, 1a is produced in modest (∼20%) yield along with a complex mixture of high MW organic products (see Supporting Information for more details). The role of the external ligand 3 is not entirely clear (and is currently under investigation), but it may serve as a trap for highly reactive cationic Pd species generated after C-C bond forming reductive elimination.