Suzuki-Miyaura cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under aerobic conditions catalyzed by palladium complexes with thiosemicarbazone ligands

Tetrahedron Letters

Volumn 46, Issue 12, 2005, Pages 1967-1970

  Kostas, Ioannis D ^a   Andreadaki, Fotini J ^a   Kovala Demertzi, Dimitra ^b   Prentjas, Christos ^b   Demertzis, Mavroudis A ^b  

^a INSTITUTE OF BIOLOGY   (Greece)

^b UNIVERSITY OF IOANNINA   (Greece)

Author keywords

C C bond formation; Homogeneous catalysis; Palladium complex; Phosphine free ligand; Suzuki Miyaura cross coupling; Thiosemicarbazone

Indexed keywords

BENZENEBORONIC ACID; BROMIDE; CHLORIDE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; ELECTRON; SUZUKI REACTION; X RAY ANALYSIS;

EID: 14644429741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.003     Document Type: Article

References (40)

1. Recent selected monographs: J. Tsuji Palladium Reagents and Catalysts 1995 John Wiley & Sons Chichester
2. F. Diederich, and P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim
3. M.T. Reetz Transition Metal Catalysed Reactions S.G. Davies S.-I. Murahashi 1999 Blackwell Science Oxford
4. N. Miyaura Cross-Coupling Reaction 2002 Springer Berlin
5. Recent selected reviews: N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
6. S.P. Stanforth Tetrahedron 54 1998 263 303
7. A. Suzuki J. Organomet. Chem. 576 1999 147 168
8. A. Suzuki J. Organomet. Chem. 653 2002 83 90
9. N. Miyaura Top. Curr. Chem. 219 2002 11 59
10. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
11. A. Zapf, and M. Beller Top. Catal. 19 2002 101 109
12. R.B. Bedford, C.S.J. Cazin, and D. Holder Coord. Chem. Rev. 248 2004 2283 2321
13. Selected examples of the Suzuki-Miyaura coupling, published in 2004: R.B. Bedford, C.S.J. Cazin, M.B. Hursthouse, M.E. Light, and V.J.M. Scordia Dalton Trans. 2004 3864 3868
14. F.Y. Kwong, W.H. Lam, C.H. Yeung, K.S. Chan, and A.S.C. Chan Chem. Commun. 2004 1922 1923
15. C. Baillie, L. Zhang, and J. Xiao J. Org. Chem. 69 2004 7779 7782
16. R.B. DeVasher, L.R. Moore, and K.H. Shaughnessy J. Org. Chem. 69 2004 7919 7927
17. A. Scrivanti, V. Beghetto, U. Matteoli, S. Antonaroli, A. Marini, F. Mandoj, R. Paolesse, and B. Crociani Tetrahedron Lett. 45 2004 5861 5864
18. R.C. Smith, R.A. Woloszynek, W. Chen, T. Ren, and J.D. Protasiewicz Tetrahedron Lett. 45 2004 8327 8330
19. M. an der Heiden, and H. Plenio Chem. Eur. J. 10 2004 1789 1797
20. A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Furmann, N. Shaikh, U. Dingerdissen, and M. Beller Chem. Commun. 2004 38 39
21. I.J.S. Fairlamb, A.R. Kapdi, J.M. Lynam, R.J.K. Taylor, and A.C. Whitwood Tetrahedron 60 2004 5711 5718
22. I.J.S. Fairlamb, A.R. Kapdi, A.F. Lee, G. Sánchez, G. López, J.L. Serrano, L. GarcIÍa, J. Pérez, and E. Pérez Dalton Trans. 2004 3970 3981
23. I.J.S. Fairlamb, A.R. Kapdi, and A.F. Lee Org. Lett. 6 2004 4435 4438
24. J.(S.) Zhou, and G.C. Fu J. Am. Chem. Soc. 126 2004 1340 1341
25. H. Palencia, F. Garcia-Jimenez, and J.M. Takacs Tetrahedron Lett. 45 2004 3849 3853
26. F. Lu, J. Ruiz, and D. Astruc Tetrahedron Lett. 45 2004 9443 9445
27. J.-H. Li, and W.-J. Liu Org. Lett. 6 2004 2809 2811
28. R.A. Gossage, H.A. Jenkins, and P.N. Yadav Tetrahedron Lett. 45 2004 7689 7691
29. G. Bringmann, C. Gunther, M. Ochse, O. Schupp, and S. Tasler W. Hertz H. Falk G.W. Kirby R. Moore Progress in the Chemistry of Organic Natural Products Vol. 82 2001 Springer New York 1 293
30. M.T. Reetz, S.R. Waldvogel, and R. Goddard Tetrahedron Lett. 38 1997 5967 5970
31. I.G. Jung, S.U. Son, K.H. Park, K.-C. Chung, J.W. Lee, and Y.K. Chung Organometallics 22 2003 4715 4720
32. I.D. Kostas, B.R. Steele, A. Terzis, and S.V. Amosova Tetrahedron 59 2003 3467 3473
33. D. Kovala-Demertzi, P.N. Yadav, M.A. Demertzis, J.P. Jasinski, F.J. Andreadaki, and I.D. Kostas Tetrahedron Lett. 45 2004 2923 2926
34. 3OPdS: C, 28.6; H, 2.4; Cl, 10.6; N, 12.5; Pd, 31.7; S, 9.5%. Found: C, 28.4; H, 2.4; Cl, 10.8; N, 12.3; Pd, 31.6; S, 9.7%
35. Known compound. Recent selected references: S. Dutta, F. Basuli, S.-M. Peng, G.-H. Lee, and S. Bhattacharya New J. Chem. 26 2002 1607 1612
36. A.D. Naik, P.A.N. Reddy, M. Nethaji, and A.R. Chakravarty Inorg. Chim. Acta 349 2003 149 158
37. J.S. Casas, E.E. Castallano, J. Ellena, M.S.G. Tasende, A. Sánchez, J. Sordo, and M.J. Vidarte Inorg. Chem. 42 2003 2584 2595
38. D. Kovala-Demertzi, M.A. Demertzis, J.P. Miller, C. Papadopoulou, C. Dodorou, and G. Filousis J. Inorg. Biochem. 86 2001 555 563
39. P.N. Yadav, M.A. Demertzis, D. Kovala-Demertzi, S. Skoulika, and D.X. West Inorg. Chim. Acta 349 2003 30 36
40. 3g