Peroxide-promoted regioselective arylation of 2-phenylpyridines and related substrates with aryl iodides

Synlett

Volumn , Issue 9, 2008, Pages 1325-1330

  Cheng, Kai ^a   Zhang, Yuhong ^a   Zhao, Jinlong ^a   Xie, Chunsong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Arylation; C H activation; Ruthenium homogeneous catalysis

Indexed keywords

BENZOYL PEROXIDE; IODINE DERIVATIVE; PEROXIDE; PYRIDINE DERIVATIVE; REAGENT; RUTHENIUM DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; METHODOLOGY; REACTION ANALYSIS;

EID: 45749095516     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072765     Document Type: Article

References (37)

1. (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004.
2. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
3. (c) Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133.
4. (a) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
5. (b) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem. Int. Ed. 2005, 44, 5384.
6. (c) Xie, C.; Zhang, Y.; Huang, Z.; Xu, P. J. Org. Chem. 2007, 72, 5431.
7. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
8. (b) Campeau, L. C.; Fagnou, K. Chem. Commun. 2006, 1253.
9. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
10. (a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem. Int. Ed. 2003, 42, 112.
11. (b) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
12. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
13. (a) Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936.
14. (b) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
15. (c) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967.
16. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
17. (e) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
18. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
19. (a) Zaitsev, V.; Shabashov, G. D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
20. (b) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
21. (c) Ferraccioli, R.; Carenzi, D.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2006, 128, 7229.
22. Giri, R.; Maugel, N.; Li, J. J.; Wang, D. H.; Breazzano, S. P.; Saunders, L. B.; Yu, J. Q. J. Am. Chem. Soc. 2007, 129, 3510.
23. (a) Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783.
24. (b) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
25. (c) Park, Y. J.; Jo, E. A.; Jun, C. H. Chem. Commun. 2005, 1185.
26. (a) Ackermann, L.; Althammer, A.; Born, R. Angew. Chem. Int. Ed. 2006, 45, 2619.
27. (b) Ackermann, L. Org. Lett. 2005, 7, 3123.
28. (c) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
29. Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
30. Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
31. Ackermann, L.; Althammer, A.; Born, R. Synlett 2007, 2833.
32. (a) Leffler, J. E.; Story, L. J. J. Am. Chem. Soc. 1967, 89, 2333.
33. (b) Wang, T. T.; Leffler, J. E. J. Org. Chem. 1971, 36, 1531.
34. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
35. Stang, P. J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc. 1988, 110, 3272.
36. 13C NMR spectra were recorded at 100 MHz, using TMS as internal standard. Mass spectrometry data of the product of direct arylation reaction were collected on an HRMS-EI instrument.
37. 2 column to afford the desired product.