Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

Journal of Organometallic Chemistry

Volumn 687, Issue 2, 2003, Pages 327-336

  Feuerstein, Marie ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Arylboronic acids; Heteroaryl halides; Palladium; Suzuki coupling; Tetraphosphine

Indexed keywords

BORONIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; FURFURAL; HALIDE; INDOLE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CONTROLLED STUDY; CROSS LINKING;

LATEOLABRAX JAPONICUS;

EID: 0344875123     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2003.07.005     Document Type: Article

References (37)

1. For a review on biaryl synthesis via cross-coupling: Stanforth S. Tetrahedron 54 1998 263
2. For examples of palladium cross-coupling with heteroaromatic compounds: Li J.J. Gribble G.W. Palladium in Heterocyclic Chemistry 2000 Pergamon Amsterdam
3. Kotha S. Lahiri K. Kashinath D. Tetrahedron 58 2002 9633
4. Suzuki A. J. Organomet. Chem. 576 1999 147
5. Suzuki A. in: Diederich F. Stang P.J. (Eds.), Metal-Catalysed Cross-Coupling Reaction 1998 Wiley New York
6. Malleron J.-L. Fiaud J.-C. Legros J.-Y. Handbook of Palladium Catalysed Organic Reactions 1997 Academic Press San Diego
7. Miyaura N. Suzuki A. Chem. Rev. 95 1995 2457
8. Beller M. Fischer H. Herrmann A. Öfele K. Brossmer C. Angew. Chem. Int. Ed. Engl. 34 1995 1848
9. D.A. Albisson, R.B. Bedford, S.E. Lawrence, P.N. Scully, J. Chem. Soc. Chem. Commun. 1998 2095
10. Wolfe J. Singer R. Yang B. Buchwald S. J. Am. Chem. Soc. 121 1999 9550
11. H. Weissman, D. Milstein, J. Chem. Soc. Chem. Commun. 1999 1901
12. Wolfe J. Buchwald S. Angew. Chem. Int. Ed. Engl. 38 1999 2413
13. Zapf A. Beller M. Chem. Eur. J. 6 2000 1830
14. Mc Guiness D. Cavell K. Organometallics 19 2000 741
15. R. Bedford, S. Welch, J. Chem. Soc. Chem. Commun. 2001 129
16. Mitchell M.B. Wallbank P.J. Tetrahedron Lett. 32 1991 2273
17. Ali N. McKillop A. Mitchell M. Rebelo R. Wallbank P. Tetrahedron Lett. 33 1992 8117
18. Zhang H. Kwong F.Y. Tian Y. Chan K.S. J. Org. Chem. 63 1998 6886
19. Sava X. Ricard L. Mathey F. Le Floch P. Organometallics 19 2000 4899
20. Liu Y. Gribble G.W. Tetrahedron Lett. 41 2000 8717
21. Littke A. Dai C. Fu G. J. Am. Chem. Soc. 122 2000 4020
22. Cooke G. Augier de Cremiers H. Rotello V. Tarbit B. Vanderstraeten P. Tetrahedron 57 2001 2787
23. Guery S. Parrot I. Rival Y. Wermuth C.G. Tetrahedron Lett. 42 2001 2115
24. Mello J.V. Finney N.S. Org. Lett. 3 2001 4263
25. Schomaker J.M. Delia T.J. J. Org. Chem. 66 2001 7125
26. Chapman G.M. Stanforth S.P. Tarbit B. Watson M.D. J. Chem. Soc. Perkin Trans. 1 2002 581
27. Parry P. Wang C. Batsanov A. Bryce M. Tarbit B. J. Org. Chem. 67 2002 7541
28. For a review on the synthesis of polypodal diphenylphosphine ligands, see: Laurenti D. Santelli M. Org. Prep. Proc. Int. 31 1999 245
29. Laurenti D. Feuerstein M. Pèpe G. Doucet H. Santelli M. J. Org. Chem. 66 2001 1633
30. M. Feuerstein, D. Laurenti, H. Doucet, M. Santelli, J. Chem. Soc. Chem. Commun. 2001 43
31. Feuerstein M. Doucet H. Santelli M. J. Org. Chem. 66 2001 5923
32. M. Feuerstein, D. Laurenti, C. Bougeant, H. Doucet, M. Santelli, J. Chem. Soc. Chem. Commun. 2001 325
33. M. Feuerstein, H. Doucet, M. Santelli, Synlett 2001 1458
34. Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett. 42 2001 5659
35. Feuerstein M. Doucet H. Santelli M. Tetrahedron Lett. 42 2001 6667
36. M. Feuerstein, F. Berthiol, H. Doucet, M. Santelli, Synlett 2002 1807
37. F. Berthiol, H. Doucet, M. Santelli, Eur. J. Org. Chem. 2003 1091