Ligand-free palladium-catalyzed direct arylation of thiazoles at low catalyst loadings

Journal of Organic Chemistry

Volumn 74, Issue 3, 2009, Pages 1179-1186

  Roger, Julien ^a   Požgan, Franc ^a   Doucet, Henri ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYLATION; CATALYST CONCENTRATIONS; CATALYST LOADINGS; LIGAND-FREE; THIAZOLE DERIVATIVES;

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; LIGANDS; PALLADIUM;

REACTION KINETICS;

1 [3 (2 PROPYLTHIAZOL 5 YL)PHENYL]ETHANONE; 1 [4 (2 PROPYLTHIAZOL 5 YL)PHENYL]PROPAN 1 ONE; 2 ETHYL 4 METHYLTHIAZOLE CARBOXYLATE DERIVATIVE; 2 ETHYL 4 METHYLTHIAZOLE DERIVATIVE; 2 N PROPYLTHIAZOLE DERIVATIVE; 4 METHYLTHIAZOLE DERIVATIVE; BROMIDE; BROMOBENZENE; CARBOXYLIC ACID DERIVATIVE; KETONE; NANOPARTICLE; PALLADIUM; PROPANE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; QUANTUM YIELD; SUZUKI REACTION;

BENZENE DERIVATIVES; BROMOBENZENES; CATALYSIS; PALLADIUM; THIAZOLES;

EID: 64549138043     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802360d     Document Type: Article

References (44)

1. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, The Netherlands, 2000.
2. Stanetty, P.; Schnuerch, M.; Mihovilovic, M. D. J. Org. Chem. 2006, 71, 3754.
3. (a) Guianvarc'h, D.; Fourrey, J.-L.; Maurisse, R.; Sun, J.-S.; Benhida, R. Org. Lett. 2002, 4, 4209.
4. (b) Haemmerle, J.; Schnuerch, M.; Stanetty, P. Synlett 2007, 2975.
5. (c) Zambon, A.; Borsato, G.; Brussolo, S.; Frascella, P.; Lucchini, V. Tetrahedron Lett. 2008, 49, 66.
6. Jensen, J.; Skjaerbaek, N.; Vedso, P. Synthesis 2001, 128.
7. Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, A.; Nakata, T.; Tani, N.; Aoyagi, Y. Heterocycles 1990, 31, 1951.
8. (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
9. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
10. (c) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
11. (d) Doucet, H.; Hierso, J. C. Curr. Opin. Drug Discovery Dev. 2007, 10, 672.
12. (e) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35.
13. (a) Roger, J.; Doucet, H. Org. Biomol. Chem. 2008, 6, 169.
14. (b) Derridj, F.; Djebbar, S.; Benali-Baitich, O.; Doucet, H. J. Organomet. Chem. 2008, 693, 135.
15. (c) Gottumukkala, A. L.; Derridj, F.; Djebbar, S.; Doucet, H. Tetrahedron Lett. 2008, 49, 2926.
16. (d) Ackermann, L.; Vincente, R.; Born, R. Adv. Synth. Catal. 2008, 350, 741.
17. (e) Besselièvre, F.; Mahuteau-Betzer, F.; Grierson, D. S.; Pigel, S. J. Org. Chem. 2008, 73, 3278.
18. (f) Martin, T.; Verrier, C.; Hoarau, C.; Marsais, F. Org. Lett. 2008, 10, 2909.
19. (g) Gottumukkala, A. L.; Doucet, H. Adv. Synth. Catal. 2008, 350, 2183.
20. For direct 5-arylations of thiazoles with palladium associated to mono-phosphine ligands see: (a) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R.; Akita, Y.; Ohta, A. Heterocycles 1992, 33, 257.
21. (b) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
22. (c) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
23. (d) Dahlgren, A.; Kvarnstrom, I.; Vrang, L.; Hamelink, E.; Hallberg, A.; Rosenquist, A.; Samuelsson, B. Bioorg. Med. Chem. 2003, 11, 827.
24. (e) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003, 59, 5685.
25. (f) Oscarsson, K.; Oscarson, S.; Vrang, L.; Hamelink, E.; Hallberg, A.; Samuelsson, B. Bioorg. Med. Chem. 2003, 11, 1235.
26. (g) Kobayashi, K.; Mohamed, A.; Mohamed, S.; Mori, A. Tetrahedron 2006, 62, 9548.
27. (h) Chiong, H. A.; Daugulis, O. Org. Lett. 2006, 9, 1449.
28. (i) Priego, J.; Gutierrez, S.; Ferritto, R.; Broughton, H. B. Synlett 2007, 2957.
29. (j) Campeau, L.-C.; Bertrand-Laperle, M.; Leclerc, J.-P.; Villemure, E.; Gorelsky, S.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276.
30. For direct 5-arylations of thiazoles with palladium associated to diphos-phine ligands see: (a) Masui, K.; Mori, A.; Okano, K.; Takamura, K.; Kinoshita, M.; Ikeda, T. Org. Lett. 2004, 6, 2011.
31. (b) Hara, O.; Nakamura, T.; Sato, F.; Makino, K.; Hamada, Y. Heterocycles 2006, 65, 1.
32. (c) Turner, G. L.; Morris, J. A.; Greaney, M. F. Aneew. Chem., Int. Ed. 2007, 46, 7996.
33. (d) Gottumukkala, A. L.; Doucet, H. Eur. J. Inorg. Chem. 2007, 3626.
34. (e) Derridj, F.; Gottumukkala, A. L.; Djebbar, S.; Doucet, H. Eur. J. Inorg. Chem. 2008, 2550.
35. (a) Battace, A.; Lemhadri, M.; Zair, T.; Doucet, H.; Santelli, M. Organometallics 2007, 26, 472.
36. (b) Battace, A.; Lemhadri, M.; Zair, T.; Doucet, H.; Santelli, M. Adv. Synth. Catal. 2007, 349, 2507.
37. (a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285.
38. (b) Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559.
39. (c) de Vries, J. G. Dalton Trans. 2006, 421.
40. Alimardanov, A.; Schmieder-van de Vondervoort, L.; de Vries, A. H. M.; de Vries, J. G. Adv. Synth. Catal. 2004, 346, 1812.
41. For direct 5-arylations of thiazoles with aryl halides, using ligand-less palladium catalysts see: Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578.
42. Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476.
43. PoZgan, F.; Roger, J.; Doucet, H. ChemSusChem 2008, 1, 404.
44. Jensen, J.; Skjaerbaek, N.; Vedso, P. Synthesis 2001, 128.