Palladium-catalyzed methylation and arylation of sp2 and sp 3 C-H bonds in simple carboxylic acids

Journal of the American Chemical Society

Volumn 129, Issue 12, 2007, Pages 3510-3511

  Giri, Ramesh ^a   Maugel, Nathan ^a   Li, Jiao Jie ^a   Wang, Dong Hui ^a   Breazzano, Steven P ^a   Saunders, Lindsey B ^a   Yu, Jin Quan ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHYLATION; ORGANIC CHEMISTRY;

EID: 33947644069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0701614     Document Type: Article

References (38)

1. For reviews see: (a) Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998.
2. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
3. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411.
4. (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
5. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
6. (d) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
7. (e) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
8. (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
9. (b) Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
10. (a) Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
11. (b) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc., 2006, 128, 12634.
12. For a Rh-catalyzed ortho arylation of 2-phenylpyridine using tetraaryltin see: Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439.
13. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
14. (b) Brown, J. M. Chem. Soc. Rev. 1993, 22, 25.
15. (c) Halpern, J. Science 1982, 217, 401.
16. (a) For a remarkable Ru-catalyzed ortho arylation of acetophenone using a phenylboronate see: Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
17. (b) For an example of Rh-catalyzed alkenylation of aryl C-H bonds directed by imine see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
18. 2 see: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
19. 2 see: Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
20. (a) Kao, L.-C.; Sen, A. J. Chem. Soc., Chem. Commun. 1991, 1242.
21. (b) Dangel, B. D.; Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2001, 123, 8149.
22. (c) Lee, J. M.; Chang, S. Tetrahedron Lett. 2006, 47, 1375.
23. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
24. 3 C-H bonds using an amide-pyridine directing group and Arl as the arylating reagent see: Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
25. 6 see: (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
26. (b) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
27. (a) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
28. (b) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
29. 2- slowly during the reaction which appears to be important for the catalysis.
30. Hermans, S.; Wenkin, M.; Devillers, M. J. Mol. Catal. A: Chem. 1998, 136, 59.
31. Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
32. 2 C-H bonds using Mel or ArX see: (a) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
33. (b) Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 286, C13.
34. (c) Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119.
35. (d) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506.
36. (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148.
37. 3 C-H bonds in 1-tert-butyl-2- iodobenzene see: Dyker, G. Angew. Chem., Int. Ed. 1992, 31, 1023.
38. The arylation of toluic acid 1 under the same conditions gives the ortho arylated product in 95% yield.