A new precatalyst for the Suzuki reaction - A pyridyl-bridged dinuclear palladium complex as a source of mono-ligated palladiuin(0)

New Journal of Chemistry

Volumn 28, Issue 5, 2004, Pages 600-605

  Beeby, Andrew ^a   Bettington, Sylvia ^a   Fairlamb, Ian J S ^b   Goeta, Andrés E ^a   Kapdi, Anant R ^b   Niemelä, Elina H ^b   Thompson, Amber L ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOPYRIDINE; 2,4 DIFLUOROPHENYLBORONIC ACID; BENZENEBORONIC ACID; BROMINE DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; ISOLATION PROCEDURE; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 2942519252     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b401077a     Document Type: Article

References (41)

1. (a) Metal-catalyzed Cross-coupling Reactions, eds. F. Diederich and P. J. Stang, Wiley-VCH, New York, 1998;
2. (b) J. Tsuji, Palladium Reagents and Catalysts, Innovations in Organic Synthesis, Wiley, New York, 1995.
3. N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483.
4. A. F. Littke and G. C. Fu, Angew. Chem., Int. Ed., 2002, 41, 4176-4211 and references cited therein.
5. A. F. Littke, C. Dai and G. C. Fu, J. Am. Chem. Soc., 2000, 122, 4020-4028.
6. 3P have been isolated and characterized, see: J. P. Stambuli, M. Buhl and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 9346-9347.
7. 3P have been isolated and characterized, see: J. P. Stambuli, M. Buhl and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 9346-9347.
8. Dibenzylideneacetone (DBA) is assumed to play a non-innocent role in Pd-catalyzed cross-coupling reactions; see: C. Amatore, G. Broeker, A. Jutand and F. Khalil, J. Am. Chem. Soc., 1997, 119, 5176-5185.
9. Complete crystallographic data for 1 have been deposited at the Cambridge Crystallographic Data Centre (deposit number, CCDC 207 524).
10. K. Nakatsu, K. Kinoshita, H. Kanda, K. Isobe, Y. Nakamura and S. Kawaguchi, Chem. Lett., 1980, 913-914.
11. T. A. Anderson, R. J. Barton and B. E. Robertson, Acta. Crystallogr., Sect. C, 1985, C41, 1171-1173.
12. F. H. Allen, Acta Crystallogr., Sect. B, 2002, B58, 380-388.
13. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson and R. Taylor, Acta Crystallogr., Sect. B, 2002, B58, 389-397.
14. The use of dimeric 2-pyridyl Pd(II) complexes as effective catalysts for Suzuki cross-coupling reactions has not been reported.
15. It is important that enough silica-gel is used to ensure that trace quantities of palladium are not carried through into the analysis sample. We have found that the reaction can still turnover on passing larger quantities of material through silica gel. In cases where larger samples are required it is possible to add two equivalents (per Pd) of 1,1′-diphenylphosphinoethane (dppe) to the crude reaction which irreversibly inhibits catalysis: E. H. Niemela, A. F. Lee and I. J. S. Fairlamb, Tetrahedron Lett., 2004, in press.
16. K. Isobe and S. Kawaguchi, Heterocycles, 1981, 16, 1603-1612.
17. C. H. C. Clavius, J. S. L. Yeo, Z. H. Loh, J. J. Vittal, W. Henderson and T. S. A. Hor, J. Chem. Soc. Dalton. Trans., 1998, 3777-3784.
18. If the reactions are opened up to air, palladium black is produced in <0.5 h.
19. 3P-Pd(0)-Br(-)). For detailed information related to this type of cycle see the work by Amatore and Jutand: (a) C. Amatore and A. Jutand, Acc. Chem. Res., 2000, 33, 314-321; (b) C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254-278.
20. 3P-Pd(0)-Br(-)). For detailed information related to this type of cycle see the work by Amatore and Jutand: (a) C. Amatore and A. Jutand, Acc. Chem. Res., 2000, 33, 314-321; (b) C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254-278.
21. N. W. Alcock, J. M. Brown and D. I. Hulmes, Tetrahedron, 1993, 4, 743-756.
22. (a) D. R. Coulson, Inorg. Synth., 1972, 13, 121-124;
23. (b) R. B. King and P. N. Kapoor, Inorg. Chem., 1972, 11, 1524-1527.
24. F. G. Mann and D. Purdie, J. Chem. Soc., 1935, 1549-1551.
25. J. P. Wolfe, R. A. Singer, B. H. Yang and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550-9561.
26. C. J. Mathews, P. J. Smith and T. Welton, Chem. Commun., 2000, 1249-1250.
27. N. E. Leadbeater and M. Marco, Org. Lett., 2002, 4, 2973-2976.
28. C. Griffiths and N. E. Leadbeater, Tetrahedron Lett., 2000, 41, 2487-2490.
29. Y. Kobayashi, A. D. William and R. Mizojiri, J. Organomet. Chem., 2002, 653, 91-97.
30. N. Kataoka, Q. Shelby, J. P. Stambuli and J. F. Hartwig, J. Org. Chem., 2002, 67, 5553-5566.
31. N. Miyaura, T. Yanagi and A. Suzuki, Synth. Commun., 1981, 11, 513-519.
32. A. F. Littke and G. C. Fu, J. Am. Chem. Soc., 2001, 123, 6989-7000.
33. K. Inada and N. Miyaura, Tetrahedron, 2000, 56, 8657-8660.
34. A. G. M. Barrett, P. A. Procopiou and U. Voigtmann, Org. Lett., 2001, 3, 3165-3168.
35. J. P. Idoux, G. E. Kiefer, G. R. Baker, W. E. Puckett and F. J. Spence, J. Org. Chem., 1980, 45, 441-444.
36. I. Klement, M. Rottlaender, C. E. Tucker, T. N. Majid and P. Knochel, Tetrahedron, 1996, 52, 7201-7220.
37. H. C. Bell, J. R. Kalman, J. T. Pinhey and S. Sternhell, Tetrahedron Lett., 1974, 15, 857-860.
38. C. G. Blettner, W. A. König, W. Stenzel and T. Schotten, Synlett, 1998, 295-297.
39. J. Cosier and A. M. Glazer, J. Appl. Cryst., 1986, 19, 105-107.
40. SMART-NT, Data Collection Software, version 5.0, Bruker Analytical X-ray Instruments Inc, Madison, Wisconsin, USA, 1999.
41. SHELXL, version 5.1, Bruker Analytical Instruments Inc, Madison, Wisconsin, USA, 1999.