Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines

Journal of Organometallic Chemistry

Volumn 694, Issue 3, 2009, Pages 455-465

  Derridj, Fazia ^a   Roger, Julien ^b   Geneste, Florence ^b   Djebbar, Safia ^a   Doucet, Henri ^b  

^a UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Aryl chlorides; C H activation; Catalysis; Heteroarenes; Palladium

Indexed keywords

ACTIVATION ANALYSIS; CHLORINE COMPOUNDS; DERIVATIVES; PALLADIUM; PLANNING; STRATEGIC PLANNING; THIOPHENE;

ARYL CHLORIDES; BENZOXAZOLE; C-H ACTIVATION; CHLOROPYRIDINES; CHLOROQUINOLINES; DIRECT COUPLINGS; H BONDS; HETEROARENES; HETEROARYLATION; LOW TO HIGHS; LOWER COSTS; STABLE CATALYSTS; THIAZOLE DERIVATIVES;

CATALYSIS;

EID: 58149512849     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.11.032     Document Type: Article

References (54)

1. For examples of palladium coupling reactions with heteroaromatic substrates:. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry (2000), Pergamon, Amsterdam
2. For selected examples of palladium-catalyzed Negishi coupling reactions of chloropyridine derivatives with heteroaryl derivatives:. Gauthier Jr. D.R., Szumigala Jr. R.H., Dormer P.G., Armstrong J.D., and Volante R.P. Org. Lett. 4 (2002) 375
3. Piersanti G., Giorgi L., Bartoccini F., Tarzia G., Minetti P., Gallo G., Giorgi F., Castorina M., Ghirardi O., and Carminati P. Org. Biomol. Chem. 5 (2007) 2567
4. L'Helgoual'ch J.-M., Seggio A., Chevallier F., Yonehara M., Jeanneau E., Uchiyama M., and Mongin F. J. Org. Chem. 73 (2008) 177
5. For examples of palladium-catalyzed Stille coupling reactions of chloropyridine derivatives with heteroaryl derivatives:. Wolf C., and Lerebours R. J. Org. Chem. 68 (2003) 7077
6. Dang Q., Rao Kasibhatla S., Reddy K.R., Jiang T., Reddy M.R., Potter S.C., Fujitaki J.M., van Poelje P.D., Huang J., Lipscomb W.N., and Erion M.D. J. Am. Chem. Soc. 129 (2007) 15491
7. Zhu G.-D., Gunawardana I.W., Boyd S.A., and Melcher L.M. J. Heterocyclic Chem. 45 (2008) 91
8. For examples of palladium-catalyzed Kumada coupling reactions of chloropyridine derivatives with heteroaryl derivatives:. Organ M.G., Abdel-Hadi M., Avola S., Hadei N., Nasielski J., O'Brien C.J., and Valente C. Chem. Eur. J. 13 (2006) 150
9. For examples of palladium-catalyzed Suzuki coupling reactions of chloropyridine derivatives with heteroaryl derivatives:. Allegretti M., Arcadi A., Marinelli F., and Nicolini L. Synlett (2001) 609
10. Duvey G., Nivoliers F., Rocca P., Godard A., Marsais F., and Queguiner G. J. Heterocyclic Chem. 38 (2001) 1039
11. Carles L., Narkunan K., Penlou S., Rousset L., Bouchu D., and Ciufolini M.A. J. Org. Chem. 67 (2002) 4304
12. Berthel S.J., Marks I.M., Yin X., Mischke S.G., Orzechowski L., Pezzoni G., Sala F., and Vassilev L.T. Anti-Cancer Drug. 13 (2002) 359
13. Ohnmacht S.A., Brenstrum T., Bleicher K.H., McNulty J., and Capretta A. Tetrahedron Lett. 45 (2004) 5661
14. Kudo N., Perseghini M., and Fu G.C. Angew. Chem., Int. Ed. 45 (2006) 1282
15. Schirok H. J. Org. Chem. 71 (2006) 5538
16. Kulkarni S.S., and Newman A.H. Bioorg. Med. Chem. Lett. 17 (2007) 2074
17. Billingsley K., and Buchwald S.L. J. Am. Chem. Soc. 129 (2007) 3358
18. Kondolff I., Doucet H., and Santelli M. J. Mol. Catal. A: Chem. 269 (2007) 110
19. Fleckenstein C.A., and Plenio H. J. Org. Chem. 73 (2008) 3236
20. For reviews on palladium-catalyzed C-H activation/functionalization of heteroaryls see:. Ritleng V., Sirlin C., and Pfeffer M. Chem. Rev. 102 (2002) 1731
21. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174
22. Satoh T., and Miura M. Chem. Lett. 36 (2007) 200
23. Doucet H., and Hierso J.-C. Curr. Opin. Drug Discover. Devel. 10 (2007) 672
24. For examples of palladium-catalyzed direct heteroarylation of bromopyridines:. Fournier Dit Chabert J., Joucla L., David E., and Lemaire M. Tetrahedron 60 (2004) 3221
25. Koubachi J., El Kazzouli S., Berteina-Raboin S., Mouaddib A., and Guillaumet G. Synlett (2006) 3237
26. Battace A., Lemhadri M., Zair T., Doucet H., and Santelli M. Adv. Synth. Catal. 349 (2007) 2507
27. Amaladass P., Clement J.A., and Mohanakrishnan A.K. Tetrahedron 63 (2007) 10363
28. Wang X., Gribkov D.V., and Sames D. J. Org. Chem. 72 (2007) 1476
29. Mohanakrishnan A.K., Amaladass P., and Clement J.A. Tetrahedron Lett. 48 (2007) 539
30. For examples of palladium-catalyzed bimolecular direct arylation of heteroaromatics by using aryl iodides:. Lane B.S., and Sames D. Org. Lett. 6 (2004) 2897
31. Cerna I., Pohl R., Klepetarova B., and Hocek M. Org. Lett. 8 (2006) 5389
32. Toure B.B., Lane B.S., and Sames D. Org. Lett. 8 (2006) 1979
33. Turner G.L., Morris J.A., and Greaney M.F. Angew. Chem., Int. Ed. 46 (2007) 7996
34. Irie M., and Takami S. J. Phys. Org. Chem. 20 (2007) 894
35. Priego J., Gutierrez S., Ferritto R., and Broughton H.B. Synlett (2007) 2957
36. For examples of palladium-catalyzed bimolecular direct arylation of heteroaromatics by using aryl chlorides:. Aoyagi Y., Inoue A., Koizumi I., Hashimoto R., Tokunaga K., Gohma K., Komatsu J., Sekine K., Miyafuji A., Kunoh J., Honma R., Akita Y., and Ohta A. Heterocycles 33 (1992) 257
37. Hodgetts K.J., and Kershaw M.T. Org. Lett. 5 (2003) 2911
38. Leclerc J.-P., and Fagnou K. Angew. Chem., Int. Ed. 45 (2006) 7781
39. David E., Pellet-Rostaing S., and Lemaire M. Tetrahedron 63 (2007) 8999
40. Gottumukkala A.L., and Doucet H. Eur. J. Inorg. Chem. (2007) 3629
41. For examples of palladium-catalyzed intramolecular direct arylation of heteroaromatics by using aryl chlorides, see:. Smet M., Van Dijk J., and Dehaen W. Synlett (1999) 495
42. Jonckers T.H.M., Maes B.U.W., Lemière G.L.F., Rombouts G., Pieters L., Haemers A., and Dommisse R.A. Synlett (2003) 615
43. Leclerc J.-P., André M., and Fagnou K. J. Org. Chem. 71 (2006) 1711
44. For examples of palladium-catalyzed direct heteroarylation of chloropyridines:. Zhuravlev F.A. Tetrahedron Lett. 47 (2006) 2929
45. Chiong H.A., and Daugulis O. Org. Lett. 9 (2007) 1449
46. Derridj F., Debbar S., Benali-Baitich O., and Doucet H. J. Organomet. Chem. 693 (2008) 135
47. Martin T., Verrier C., Hoarau C., and Marsais F. Org. Lett. 10 (2008) 2909
48. Cantat T., Génin E., Giroud C., Meyer G., and Jutand A. J. Organomet. Chem. 687 (2003) 365
49. Battace A., Lemhadri M., Zair T., Doucet H., and Santelli M. Organometallics 26 (2007) 472
50. Derridj F., Gottumukkala A.L., Debbar S., and Doucet H. Eur. J. Inorg. Chem. (2008) 2550
51. Gottumukkala A.L., Derridj F., Djebbar S., and Doucet H. Tetrahedron Lett. 49 (2008) 2926
52. Gottumukkala A.L., and Doucet H. Adv. Synth. Catal. 350 (2008) 2183
53. Pozgan F., Roger J., and Doucet H. ChemSusChem 1 (2008) 404
54. Savarino P., Viscardi G., Quagliotto P., Perracino P., and Barni E. J. Heterocyclic Chem. 34 (1997) 1479