Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

Canadian Journal of Chemistry

Volumn 82, Issue 2, 2004, Pages 206-214

  Friesen, Richard W ^a   Trimble, Laird A ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

Boronic acids; Cross coupling; Palladium; Quinolines; Regioselectivity

Indexed keywords

AMMONIUM COMPOUNDS; CATALYSIS; OPTIMIZATION; ORGANIC ACIDS; WATER;

4,7-DICHLOROQUINOLINE; ARYLCORONIC ACIDS; PHENYLBORONIC ACID; SUZUKI CROSS-COUPLING REACTIONS;

PALLADIUM COMPOUNDS;

4,7 DICHLOROQUINOLINE; 7 CHLORO 4 IODOQUINOLINE; 7 CHLORO 4 PHENYLQUINOLINE; BENZENEBORONIC ACID; DIPHENYLQUINOLINE; PALLADIUM; PHOSPHINE; QUINOLINE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HEAT TREATMENT; INTERMETHOD COMPARISON; QUANTUM YIELD; SUZUKI REACTION;

EID: 2342625972     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-187     Document Type: Article

References (31)

1. N. Miyaura and A. Suzuki. Chem. Rev. 95, 2457 (1995).
2. S.P. Stanforth. Tetrahedron, 54, 263 (1998).
3. A. Suzuki. J. Organomet. Chem. 653, 83 (2002).
4. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire. Chem. Rev. 102, 1359 (2002).
5. N. Miyaura. Topics Curr. Chem. 219, 5 (2002).
6. N.M. Ali, A. McKillop, M.B. Mitchell, R.A. Rebelo, and P.J. Wallbank. Tetrahedron, 48, 8117 (1992).
7. M.A. Ciufolini, J.W. Mitchell, and F. Roschangar. Tetrahedron Lett. 37, 8281 (1996).
8. O. Lohse, P. Thevenin, and E. Waldvogel. Synlett, 45 (1999).
9. Y. Gong and H.W. Pauls. Synlett, 829 (2000).
10. M. Allegretti, A. Arcadi, F. Marinelli, and L. Nicolini. Synlett, 609 (2001).
11. A.F. Littke and G.C. Fu. Angew. Chem. Int. Ed. 41, 4176 (2002).
12. D. Dubé, M. Blouin, C. Brideau, C.-C. Chan, S. Desmarais, D. Ethier, J.-P. Falgueyret, R.W. Friesen, M. Girard, Y. Girard, J. Guay, D. Riendeau, P. Tagari, and R.N. Young. Bioorg. Med. Chem. Lett. 8, 1255 (1998).
13. J.-Y. Legros, G. Primault, and J.-C. Fiaud. Tetrahedron, 57, 2507 (2001).
14. D. Najiba, J.-F. Carpentier, Y. Castanet, C. Biot, J. Brocard, and A. Mortreux. Tetrahedron Lett. 40, 3719 (1999).
15. A.S. Bhanu Prasad, T.M. Stevenson, J.R. Citineni, V. Nyzam, and P. Knochel. Tetrahedron, 53, 7237 (1997).
16. T. Shiota and T. Yamamori. J. Org. Chem. 64, 453 (1999).
17. J.M. Nolan and D.L. Comins. J. Org. Chem. 68, 3736 (2003).
18. R.M. Peck, R.K. Preston, and H.J. Creech. J. Am. Chem. Soc. 81, 3984 (1959).
19. T.I. Wallow and B.M. Novak. J. Org. Chem. 59, 5034 (1994).
20. C.R. LeBlond, A.T. Andrews, Y. Sun, and J.R. Sowa, Jr. Org. Lett. 3, 1555 (2001).
21. D. Badone, M. Baroni, R. Cardamone, A. Ielmini, and U. Guzzi. J. Org. Chem. 62, 7170 (1997).
22. N.B. Leadbeater and M. Marco. J. Org. Chem. 68, 888 (2003).
23. R.F. Heck. Palladium reagents in organic syntheses. Academic Press, London. 1985. p. 184.
24. G.B. Smith, G.G. Dezeny, D.L. Hughes, A.O. King, and T.R. Verhoeven. J. Org. Chem. 59, 8151 (1994).
25. A.F. Littke, C. Dai, and G.G. Fu. J. Am. Chem. Soc. 122, 4020 (2000).
26. A.-S. Castanet, F. Colobert, J.-R. Desmurs, and T. Schlama. J. Mol. Catalysis A Chem. 182-183, 481 (2002).
27. C. Amatore and A. Jutand. J. Organomet. Chem. 576, 254 (1999).
28. C. Amatore and A. Jutand. Acc. Chem. Res. 33, 314 (2000).
29. K. Fagnou and M. Lautens. Angew. Chem. Int. Ed. 41, 26 (2002).
30. P.M. Maitlis. The organic chemistry of palladium. Vol 1. Academic Press, New York. 1971. Chap 1.
31. S. Tasler and B.H. Lipshutz. J. Org. Chem. 68, 1190 (2003).