Palladium-catalyzed direct oxidative alkenylation of azoles

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5421-5424

  Miyasaka, Mitsuru ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLATION; GOOD YIELD;

OLEFINS;

PALLADIUM;

ALKENE DERIVATIVE; ALKENYL GROUP; AROMATIC COMPOUND; OXIDIZING AGENT; PALLADIUM; PYRROLE DERIVATIVE; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77955126836     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101214y     Document Type: Article

References (45)

1. For reviews of transition-metal-catalyzed C-H activation, see: Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
2. Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200
3. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
4. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
5. Campeau, L. C.; Stuart, D. R.; Fagnou, K. Aldrichchim. Acta 2007, 40, 35
6. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
7. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
8. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
9. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
10. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
11. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
12. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
13. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
14. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
15. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
16. Karimi, B.; Behzadnia, H.; Elhamifar, D.; Akhavan, P. F.; Esfahani, F. K.; Zamani, A. Synthesis 2010, 1399
17. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211
18. Boele, M. D. K.; van Strijdonck, G. P. J.; de Vries, A. M. H.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586
19. Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
20. Wang, J.-R.; Yang, C.-T.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 5449
21. Fujiwara, Y.; Maruyama, O.; Yoshidomi, M.; Taniguchi, H. J. Org. Chem. 1981, 46, 851
22. Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097
23. Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854
24. Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125
25. Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528
26. Garcia-Rubia, A.; Arrayas, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6511
27. Aouf, C.; Thiery, E.; Bras, J. L.; Muzart, J. Org. Lett. 2009, 11, 4096
28. Zhao, J.; Huang, L.; Cheng, K.; Zhang, Y. Tetrahedron Lett. 2009, 50, 2758
29. Yang, Y.; Cheng, K.; Zhang, Y. Org. Lett. 2009, 11, 5606
30. Maehara, A.; Satoh, T.; Miura, M. Tetrahedron 2008, 64, 5982
31. Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159
32. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
33. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
34. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506
35. There are only two precedents for the direct alkenylation of pyrazole and imidazo[1,2- a ]pyridine: Itahara, T.; Kawasaki, K.; Ouseto, F. Bull. Chem. Soc. Jpn. 1984, 57, 3488
36. Koubachi, J.; Raboin, S. B.; Mouaddib, A.; Guillaumet, G. Synthesis 2009, 271
37. Gottumukkala, A. L.; Derridj, F.; Djebbar, S.; Doucet, H. Tetrahedron Lett. 2008, 49, 2926
38. Besselievre, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029
39. Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074
40. Liang, Z.; Zhao, J.; Zhang, Y. J. Org. Chem. 2010, 75, 170
41. Hiraki, K.; Fuchita, Y.; Takakura, S. J. Organomet. Chem. 1981, 210, 273
42. This is probably because the methyl group at 4-position in thiazole inhibited the unfavorable coordination of nitrogen to the palladium center necessary for the competitive cyclopalladation.
43. Selected examples: Shu, C.-F.; Wang, Y.-K. J. Mater. Chem. 1998, 8, 833
44. Eckert, K.; Schröder, A.; Hartmann, H. Eur. J. Org. Chem. 2000, 1327
45. The fact that the alkenylation of azoles 1 and 4a occurs selectively at the relatively electrophile-susceptible 5-position rather than the 4-position is consistent with the relevant Pd-catalyzed direct arylation chemistry. (1a-1e)