Palladium on activated carbon - A recyclable catalyst for Suzuki-Miyaura cross-coupling of aryl chlorides in water

Synthesis

Volumn , Issue 4, 2006, Pages 692-698

  Lysén, Morten ^a,b   Köhler, Klaus ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Aryl chlorides; Biaryls; Cross coupling; Palladium; Water

Indexed keywords

ACTIVATED CARBON; CATALYST ACTIVITY; CATALYSTS; CHLORINE COMPOUNDS; FILTRATION; WATER;

ARYL BORONIC ACIDS; ARYL CHLORIDES; BIARYLS; CROSS-COUPLING;

PALLADIUM;

ACTIVATED CARBON; BORONIC ACID DERIVATIVE; CHLORIDE; PALLADIUM; WATER;

ARTICLE; CATALYST; FILTRATION; PRODUCTIVITY; REACTION ANALYSIS; RECYCLING; SUZUKI REACTION;

EID: 33644550006     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926305     Document Type: Article

References (44)

1. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
2. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
4. (a) Stanford, S. P. Tetrahedron 1998, 54, 263.
5. (b) Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verthoeven, T. R. J. Org. Chem. 1994, 59, 8151.
6. (a) For a recent review, see: Bellina, F.; Carpita, A.; Rozzi, R. Synthesis 2004, 2419.
7. (b) See also: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
8. Shaughnessy, K. H.; DeVasher, R. B. Curr. Org. Chem. 2005, 9, 585.
9. (a) Badone, D.; Baroni, R.; Cardamone, A.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
10. (b) Arcadi, A.; Cerichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. Eur. J. Org. Chem. 2003, 4080.
11. (c) Lu, G.; Franzén, R.; Zhang, Q.; Xu, Y. Tetrahedron Lett. 2005, 46, 4255.
12. (d) Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. J. Org. Chem. 2005, 70, 161.
13. (a) Arvela, K. R.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
14. (b) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
15. (c) Bedford, R. B.; Blake, M. E.; Butts, C. P.; Holder, D. Chem. Commun. 2003, 466.
16. Lysén, M.; Köhler, K. Synlett 2005, 1671.
17. (a) Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J.; Köhler, K. J. Mol. Catal. A: Chem. 2002, 182-183, 499.
18. (b) Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249.
19. Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118.
20. Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559.
21. Wright, W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
22. Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412.
23. (a) Chaumeil, H.; Signorella, S.; Drian, C. L. Tetrahedron 2000, 56, 9655.
24. (b) Kristensen, J. L.; Lysén, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435.
25. (c) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
26. (a) Vedejs, J.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
27. (b) Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867.
28. (c) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.
29. Pröckl, S. S.; Kleist, W.; Gruber, M. A.; Köhler, K. Angew. Chem. Int. Ed. 2004, 43, 1881.
30. de Vries, A. H. M.; Parlevliet, F. J.; Vondervoort, L. S.; Mommers, J. H. M.; Henderickx, H. J. W.; Walet, M. A. M.; de Vries, J. G. Adv. Synth. Catal. 2002, 344, 996.
31. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
32. Leadbeater, N. J. Org. Chem. 2001, 66, 7539.
33. Zapf, A.; Beller, M. Chem. Eur. J. 2000, 6, 1830.
34. Riggleman, S.; DeShong, P. J. Org. Chem. 2003, 68, 8106.
35. Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. J. Chem. Soc., Perkin Trans, 1 1984, 10, 2255.
36. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
37. Kabalka, G. W.; Wang, L.; Pagni, R. M.; Hair, M. C.; Namboodiri, V. Synthesis 2003, 217.
38. Nájera, C.; Gil-Molto, J.; Karlström, S.; Falvello, L. R. Org. Lett. 2003, 5, 1451.
39. Herndon, J. W.; McMullen, L. A. J. Organomet. Chem. 1989, 368, 83.
40. Li, J.-L.; Liu, N.-J. Org. Lett. 2004, 6, 2809.
41. Downie, I. M.; Hearey, H.; Kemp, G.; King, D.; Wosley, M. Tetrahedron 1992, 48, 4005.
42. Hermann, E. C.; Hoyer, G.-A.; Kelm, J. Spectrochim. Acta, Part A 1982, 38, 1057.
43. Enokido, T.; Fugami, K.; Endo, M.; Kameyama, M.; Kosugi, M. Adv. Synth. Catal. 2004, 346, 1685.
44. Denmark, S. E.; Ober, M. H. Org. Lett. 2003, 5, 1357.