Efficient heterogeneous palladium-montmorillonite catalysts for heck coupling of aryl bromides and chlorides

Synlett

Volumn , Issue 18, 2006, Pages 3130-3134

  Molnár, Árpád ^a   Papp, Attila ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

C C coupling; Heck reaction; Heterogeneous catalysts; Montmorillonite; Palladium

Indexed keywords

BROMIDE; CHLORIDE; HALIDE; MONTMORILLONITE; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; HECK REACTION;

EID: 33751280966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951493     Document Type: Article

References (75)

1. (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
2. (b) Bräse, S.; de Meijere, S. A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 3, 99.
3. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
4. (a) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 2, 49.
5. (b) Suzuki, A. Chem. Commun. 2005, 4759.
6. Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 5, 203.
7. (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
8. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031.
9. (c) Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577.
10. (d) Consorti, C. S.; Ebeling, G.; Flores, F. R.; Rominger, F.; Dupont, J. Adv. Synth. Catal. 2004, 346, 617.
11. (e) Frey, G. D.; Schütz, J.; Herdtweck, E.; Herrmann, W. A. Organometallics 2005, 24, 4416.
12. (f) Yi, C.; Hua, R. Tetrahedron Lett. 2006, 47, 2573.
13. (g) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 125, 581.
14. (a) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
15. (b) Bedford, R. B. Chem. Commun. 2003, 1787.
16. (c) Yao, Q.; Kinney, E. P.; Zheng, C. Org. Lett. 2004, 6, 2997.
17. (d) Zapf, A.; Beller, M. Chem. Commun. 2005, 431.
18. (e) Yu, K. Q.; Sommer, W.; Richardson, J. M.; Week, M.; Jones, C. W. Adv. Synth. Catal. 2005, 347, 161.
19. (f) Bergbreiter, D. E.; Osburn, P. L.; Frels, J. D. Adv. Synth. Catal. 2005, 347, 172.
20. Recent examples: (a) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134.
21. (b) Bennur, T. H.; Ramani, A.; Bal, R.; Chanda, B. M.; Sivasanker, S. Catal. Commun. 2002, 3, 493.
22. (c) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
23. (d) Srivastava, R.; Venkatathri, N.; Srinivas, D.; Ratnasamy, P. Tetrahedron Lett. 2003, 44, 3649.
24. (e) Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
25. (f) Li, L.; Shi, J.-L.; Van, J.-N. Chem. Commun. 2004, 1990.
26. (g) Crudden, C. M.; Sateesh, M.; Lewis, R. J. Am. Chem. Soc. 2005, 127, 10045.
27. (h) Wang, L.; Zhang, Y.; Xie, C. Synlett 2005, 1861.
28. Recent examples: (a) Caló, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Organometallics 2004, 23, 5154.
29. (b) Cassol, C. C.; Umpierre, A. P.; Machado, G.; Wolke, S. I.; Dupont, J. J. Am. Chem. Soc. 2005, 127, 3298.
30. (c) Bhattacharya, S.; Srivastava, A.; Sengupta, S. Tetrahedron Lett. 2005, 46, 3557.
31. (d) Gniewek, A.; Trzeciak, A. M.; Ziolkowski, J. J.; Kȩpiń ski, L.; Wrzyszcz, J.; Tylus, W. J. Catal. 2005, 229, 332.
32. (e) Luo, C.; Zhang, Y.; Wang, Y. J. Mol. Catal. A: Chem. 2005, 229, 7.
33. (f) Houdayer, A.; Schneider, R.; Billaud, D.; Ghanbaja, J.; Lambert, J. Appl. Organomet. Chem. 2005, 19, 1239.
34. (g) Li, S.; Lin, Y.; Xie, H.; Zhang, S.; Xu, J. Org. Lett. 2006, 8, 391.
35. (h) de Vries, J. G. Dalton Trans. 2006, 421.
36. (a) Pröckl, S. S.; Kleist, W.; Gruber, M. A.; Köhler, K. Angew. Chem. Int. Ed. 2004, 43, 1881.
37. (b) Pröckl, S. S.; Kleist, W.; Köhler, K. Tetrahedron 2005, 61, 9855.
38. (a) Mastalir, Á.; Király, Z.; Berger, F. Appl. Catal., A 2004, 269, 161.
39. (b) Mastalir, Á.; Király, Z.; Szöllösi, G.; Bartók, M. Appl. Catal., A 2001, 213, 133.
40. (c) Mastalir, Á.; Király, Z.; Szöllösi, G.; Bartók, M. J. Catal. 2000, 194, 146.
41. (a) Ramchandani, R. K.; Uphade, B. S.; Vinod, M. P.; Wakharkar, R. D.; Choudhary, V. R.; Sudalai, A. Chem. Commun. 1997, 2071.
42. (b) Varma, R. S.; Naicker, K. P.; Liesen, P. J. Tetrahedron Lett. 1999, 40, 2075.
43. Poyatos, M.; Márquez, F.; Peris, E.; Claver, C.; Fernandez, E. New J. Chem. 2003, 27, 425.
44. Waterlot, C.; Couturier, D.; Rigo, B. Tetrahedron Lett. 2000, 41, 317.
45. (a) Molnár, Á.; Papp, A.; Miklós, K.; Forgo, P. Chem. Commun. 2003, 2626.
46. (b) Papp, A.; Miklós, K.; Forgo, P.; Molnár, Á. J. Mol. Catal. A: Chem. 2005, 229, 107.
47. Papp, A.; Tóth, D.; Molnár, Á. React. Kinet. Catal. Lett. 2006, 87, 335.
48. Papp, A.; Galbács, G.; Molnár, A. Tetrahedron Lett. 2005, 46, 7725.
49. 2O (0.33 g) dissolved in water was added to Na-montmorillonite (5 g). After stirring for 4 h the solid was separated by centrifugation and washed thoroughly with water. Finally, the wet products were oven-dried (95 °C, 1 Torr, 6 h). The palladium content was determined by means of inductively coupled plasma atomic emission spectroscopy (ICP-AES). Catalysts used in recycling experiments were reduced in flowing hydrogen (200 °C, 2 h).
50. Cracker, M.; Herold, R. H. M. J. Mol. Catal. 1991, 70, 209.
51. 1H NMR (Bruker Avance DRX 500).
52. Jeffery, T. Tetrahedron 1996, 52, 10113.
53. (a) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39.
54. (b) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990.
55. (c) Mukhopadhyay, S.; Rothenberg, G.; Joshi, A.; Baidossi, M.; Sasson, Y. Adv. Synth. Catal. 2002, 344, 348.
56. (d) Zhao, F.; Arai, M. React. Kinet. Catal. Lett. 2004, 81, 281.
57. (a) Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249.
58. (b) Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
59. (a) Zhao, F.; Shirai, M.; Ikushima, Y.; Arai, M. J. Mol. Catal. A: Chem. 2000, 154, 39.
60. (b) Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. Chem. Eur. J. 2000, 6, 843.
61. (c) Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J.; Köhler, K. J. Mol. Catal. A: Chem. 2002, 182-183, 499.
62. (d) Dams, M.; Drijkoningen, L.; Pauwels, B.; Van Tendeloo, G.; De Vos, D. E.; Jacobs, P. A. J. Catal. 2002, 209, 225.
63. (e) Schmidt, A. F.; Smirnov, V. V. J. Mol. Catal. A: Chem. 2003, 203, 75.
64. (f) Ambulgekar, G. V.; Bhanage, B. M.; Samant, S. D. Tetrahedron Lett. 2005, 46, 2483.
65. (g) Ji, Y.; Jain, S.; Davis, R. J., Jr. J. Phys. Chem. B 2005, 109, 17232.
66. (a) Zhao, F.; Shirai, M.; Ikushima, Y.; Arai, M. J. Mol. Catal. A: Chem. 2002, 180, 211.
67. (b) Zhao, F.; Murakami, K.; Shirai, M.; Arai, M. J. Catal. 2000, 194, 479.
68. (a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285.
69. (b) Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559.
70. (a) Leadbeater, N. E.; Marco, M. Angew. Chem. Int. Ed. 2003, 42, 1407.
71. (b) Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
72. (a) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
73. (b) Caporusso, A. M.; Innocenti, P.; Aronica, L. A.; Vitulli, G.; Gallina, R.; Biffis, A.; Zecca, M.; Corain, B. J. Catal. 2005, 234, 1.
74. 3 (0.5 mmol)], and Pd catalyst (0.3 mol%) were reacted in NMP (2 mL). Catalyst samples after reaction were separated by centrifugation, washed successively with acetone, water, acetone and, finally, dried under an infra lamp and reused.
75. Palczewska, W. Adv. Catal. 1975, 24, 245.