Palladium-catalyzed direct arylation of heteroaromatic compounds: Improved conditions utilizing controlled microwave heating

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8138-8142

  Baghbanzadeh, Mostafa ^a   Pilger, Christian ^b   Oliver Kappe, C ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYLATIONS; CATALYST LOADINGS; HETEROAROMATIC COMPOUNDS; HETEROCYCLES; MICROWAVE-ASSISTED;

BROMINE COMPOUNDS; CATALYSIS;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; BENZOTHIOPHENE; BROMINE DERIVATIVE; HETEROCYCLIC COMPOUND; PALLADIUM ACETATE;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; MICROWAVE COOKING;

EID: 80054117910     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201516v     Document Type: Article

References (51)

1. (a) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 20, 3382.
2. (b) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
3. (c) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
4. (d) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
5. (e) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
6. (f) Roger, J.; Gottumukkala, A. L.; Doucet, H. Chem Cat Chem 2010, 2, 20.
7. (a) Jin, Z. Nat. Prod. Rep. 2003, 20, 584.
8. (b) Gompel, M.; Leost, M.; De Kier Joffe, E. B.; Puricelli, L.; Franco, L. H.; Palermo, J.; Meijer, L. Bioorg. Med. Chem. Lett. 2004, 14, 1703.
9. (a) Golebiowski, A.; Klopfenstein, S. R.; Portlock, D. E. Curr. Opin. Chem. Biol. 2001, 5, 273.
10. (b) Kitagawa, H.; Ozawa, T.; Takahata, S.; Iida, M.; Saito, J.; Yamada, M. J. Med. Chem. 2007, 50, 4710.
11. see: (a) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383.
12. (b) Nakamura, N.; Tajima, Y.; Sakai, K. Heterocycles 1982, 17, 235.
13. (c) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919.
14. (d) Akita, Y.; Inoue, A.; Yamamoto, K.; Ohta, A.; Kurihara, T.; Shimizu, M. Heterocycles 1985, 23, 2327.
15. see: (a) Beccalli, E. M; Broggini, G.; Martinelli, M.; Paladino, G.; Zoni, C. Eur. J. Org. Chem. 2005, 2091.
16. (b) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Synthesis 2008, 136.
17. (c) Basolo, L.; Beccalli, E. M.; Borsini, E.; Broggini, G. Tetrahedron 2009, 65, 3486.
18. (d) Potavathri, S.; Pereira, K. C.; Gorelsky, S. I.; Pike, A.; LeBris, A. P.; DeBoef, B. J. Am. Chem. Soc. 2010, 132, 14676.
19. (e) Nadres, E. T.; Lazareva, A.; Daugulis, O. J. Org. Chem. 2011, 76, 471.
20. (f) Wagner, A. M.; Sanford, M. S. Org. Lett. 2011, 13, 288.
21. (g) Roy, D.; Mom, S.; Lucas, D.; Cattey, H.; Hierso, J.-C.; Doucet, H. Chem.-Eur. J. 2011, 17, 6453.
22. (h) Beydoun, K.; Doucet, H. J. Organomet. Chem. 2011, 696, 1749.
23. (i) Chen, L.; Roger, J.; Bruneau, C.; Dixneuf, P. H.; Doucet, H. Chem. Commun. 2011, 47, 1872.
24. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
25. Liegault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K. J. Org. Chem. 2009, 74, 1826.
26. see: Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118.
27. (a) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
28. (b) Sun, H.-Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L. C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180.
29. (c) Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 3308.
30. see: Ackermann, L. Chem. Rev. 2011, 111, 1315.
31. see: Kappe, C. O.; Dallinger, D. Mol. Diversity 2009, 13, 71.
32. see: Obermayer, D.; Kappe, C. O. Org. Biomol. Chem. 2010, 8, 114.
33. (a) Obermayer, D.; Gutmann, B.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 8321.
34. (b) Gutmann, B.; Obermayer, D.; Reichart, B.; Prekodravac, B.; Irfan, M.; Kremsner, J. M.; Kappe, C. O. Chem.-Eur. J. 2010, 16, 12182.
35. (a) Bellina, F.; Cauteruccio, S.; Fiore, A. D.; Marchetti, C.; Rossi, R. Tetrahedron 2008, 64, 6060.
36. (b) Shibahara, F.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2011, 76, 2680.
37. (a) Liu, Y.; Zhang, S.; Abreu, P. J. M. Nat. Prod. Rep. 2006, 23, 630.
38. (b) Hughes, R. A.; Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 7930.
39. Li, G.; Kakarla, R.; Gerritz, S. W. Tetrahedron Lett. 2007, 48, 4595.
40. Kitamura, Y.; Sako, S.; Tsutsui, A.; Monguchi, Y.; Maegawa, T.; Kitade, Y.; Sajiki, H. Adv. Synth. Catal. 2010, 352, 718.
41. Molander, G. A.; Beaumard, F. Org. Lett. 2010, 12, 4022.
42. Van Leusen, A. M.; Wildeman, J.; Oldenzie, O. H. J. Org. Chem. 1977, 42, 1153.
43. Roger, J.; Doucet, H. Tetrahedron 2009, 65, 9772.
44. Roy, D.; Mom, S.; Beaupérin, M.; Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2010, 49, 6650.
45. Join, B.; Yamamoto, T.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 3644.
46. Louaisil, N.; Pham, P. D.; Boeda, F.; Faye, D.; Castanet, A.-S.; Legoupy, S. Eur. J. Org. Chem. 2011, 143.
47. Huang, J.; Chan, J.; Chen, Y.; Borths, C. J.; Baucom, K. D.; Larsen, R. D.; Faul, M. M. J. Am. Chem. Soc. 2010, 132, 3674.
48. Seggio, A.; Jutand, A.; Priem, G.; Mongin, F. Synlett 2008, 2955.
49. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
50. McLoughlin, P. T. F.; Clyne, M. A.; Aldabbagh, F. Tetrahedron 2004, 60, 8065.
51. Kaniskan, N.; Elmali, D.; Civcir, P. U. ARKIVOC 2008, xii, 17