Synthesis of Aryl Ketones by the Pd-Catalyzed C-H Activation of Arenes and Intermolecular Carbopalladation of Nitriles

Journal of the American Chemical Society

Volumn 126, Issue 8, 2004, Pages 2302-2303

  Zhou, Chengxiang ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; KETONE DERIVATIVE; NITRILE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 1542345321     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038687l     Document Type: Article

References (30)

1. (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
2. (b) Ritleng, V.; Sirlin, C.; Preffer, M. Chem. Rev. 2002, 102, 1731.
3. (a)Tsukada, N.; Mitsuboshi, T.; Setoguchi, H.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 12102.
4. (b) 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.
5. (c) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
6. (d) Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
7. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633 and references therein.
8. Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771.
9. (a) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: New York, 1995.
10. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi. E., Ed.: John Wiley & Sons: New York, 2002.
11. (a) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238.
12. (b) Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133.
13. (c) Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9276.
14. (d) Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2002, 67, 9428.
15. (e) Tian, Q.; Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2003, 68, 339.
16. (f) Yang, C. C.; Tai, H. M.; Sun, P. J. J. Chem. Soc., Perkin. Trans. 1 1997, 2843.
17. (g) Luo, F. H.; Chu, C. I.; Cheng, C. H. Organometallics 1998, 17, 1025.
18. (h) Zhao, L.; Lu, X. Angew Chem., Int. Ed. 2002, 41, 4343.
19. For a Pd(II)-assisted Ritter reaction, see: Hegedus, L. S.; Mulhem, T. A.; Asada, H. J. Am. Chem. Soc. 1986, 108, 6224.
20. (a) Bancroft, D. P.; Cotton, F. A.; Verbruggen, M. Acta Crystallogr., Sect. C 1989, 45, 1289.
21. (b) van Benthem, R. A. T. M.; Hiemstra, H.; van Leeuwen, P. W. N. M.; Geus, J. W.; Speckamp, W. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 457.
22. (a) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
23. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185.
24. (c) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.
25. 3 (20%), have been employed as catalysts, but none of them provided any of the desired ketone product.
26. For the Houben-Hoesch reaction, see: (a) Spoerri, P. E.; DuBois, A. S. Org. React. 1949, 5, 387.
27. (b) Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 3037.
28. 3 solutions.
29. For recent examples, see: (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
30. (b) Oh, C.; Jung, H.; Kim, K.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805.