Reusable functionalized polysiloxane-supported palladium catalyst for Suzuki–Miyaura cross-coupling

Journal of Catalysis

Volumn 282, Issue 2, 2011, Pages 270-277

  Borkowski, T ^a   Zawartka, W ^a   Pospiech, P ^b   Mizerska, U ^b   Trzeciak, A M ^a   Cypryk, M ^b   Tylus, W ^c  

^a UNIVERSITY OF WROC AW   (Poland)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^c WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Immobilized catalyst; Microwave heating; Palladium; Palladium nanoparticles; Polysiloxane support; Suzuki Miyaura reaction

Indexed keywords

CATALYSIS; COMPUTER SOFTWARE REUSABILITY; MICROWAVE HEATING; NANOPARTICLES; PALLADIUM; PALLADIUM COMPOUNDS; SILICONES;

CATALYTIC PROCESS; CATALYTIC REACTIONS; IMMOBILIZED CATALYSTS; PALLADIUM CATALYST; PALLADIUM NANOPARTICLES; PHENYLBORONIC ACIDS; RECYCLING EXPERIMENTS; SUPPORTED PALLADIUM CATALYSTS;

CATALYSTS;

EID: 84861354067     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2011.06.023     Document Type: Article

References (79)

1. Yin, L., Liebscher, J., Chem. Rev., 107, 2007, 133.
2. Polshettiwar, V., Len, C., Fihri, A., Coord. Chem. Rev., 253, 2009, 2599.
3. Polshettivar, V., Molnar, A., Tetrahedron, 63, 2007, 6949.
4. Buchmeiser, M.R., (eds.) Polymeric Materials in Organic Synthesis, 2003, Wiley-VCH, Weinheim.
5. Panster, P., Wieland, S., Cornils, B., Herrmann, W.A., (eds.) Applied Homog. Catal. with Organomet. Comp. A. Comprehensive Handbook in Two Volumes, 1996, VCH, Weinheim, New York, Barel, Cambridge, Tokyo.
6. Phan, N.T.S., van der Sluys, M., Jones, C.W., Adv. Synth. Catal., 348, 2006, 609.
7. Papp, A., Galbacs, G., Molnar, A., Tetrahedron Lett., 46, 2005, 7725.
8. Biffis, A., Zecca, M., Basato, M., Eur. J. Inorg. Chem., 2001, 1131.
9. Pryjomska-Ray, I., Gniewek, A., Trzeciak, A.M., Ziółkowski, J.J., Tylus, W., Topics Catal., 40, 2006, 173.
10. Gniewek, A., Ziółkowski, J.J., Trzeciak, A.M., Zawadzki, M., Grabowska, H., Wrzyszcz, J., J. Catal., 254, 2008, 121.
11. Pröckl, S.S., Kleist, W., Gruber, M.A., Köhler, K., Angew. Chem. Int. Ed., 43, 2004, 1881.
12. Kleist, W., Lee, J.-K., Köhler, K., Eur. J. Inorg. Chem., 2009, 261.
13. Cwik, A., Hell, Z., Figueras, F., Adv. Synth. Catal., 348, 2006, 523.
14. Djakovitch, L., Köhler, K., J. Am. Chem. Soc., 123, 2001, 5990.
15. Djakovitch, L., Wagner, M., Hartung, C.G., Beller, M., Köhler, K., J. Mol. Catal. A: Chem., 219, 2004, 121.
16. Noël, S., Luo, C., Pinel, C., Djakovitch, L., Adv. Synth. Catal., 349, 2007, 1128.
17. Monopoli, A., Nacci, A., Calo, V., Ciminale, F., Cotugno, P., Mangone, A., Giannossa, L.C., Azzone, P., Cioffi, N., Molecules, 15, 2010, 5411.
18. Pröckl, S.S., Kleist, W., Köhler, K., Tetrahedron, 61, 2005, 9855.
19. Mieczyńska, E., Trzeciak, A.M., Molecules, 15, 2010, 2166.
20. Mieczyńska, E., Gniewek, A., Pryjomska-Ray, I., Trzeciak, A.M., Grabowska, H., Zawadzki, M., Appl. Catal. A: Gen., 393, 2011, 195.
21. Choudary, B.M., Mahdi, S., Chowdari, N.S., Kantam, M.L., Sreedhar, B., J. Am. Chem. Soc., 124, 2002, 14127.
22. Calo, V., Nacci, A., Monopoli, A., Fornaro, A., Sabbatini, L., Cioffi, N., Ditaranto, N., Organometallics, 23, 2004, 5154.
23. Trzeciak, A.M., Ziółkowski, J.J., Coord. Chem. Rev., 249, 2005, 2308.
24. Trzeciak, A.M., Ziółkowski, J.J., Coord. Chem. Rev., 251, 2007, 1281.
25. Cai, M., Xu, Q., Huang, Y., J. Mol. Catal. A: Chem., 271, 2007, 93.
26. Paul, S., Clark, J.H., J. Mol. Catal. A: Chem., 215, 2004, 107.
27. Yang, Q., Ma, S., Li, J., Xiao, F., Xiong, H., Chem. Commun., 2008, 2495.
28. Webb, J.D., MacQuarrie, S., McEleney, K., Crudden, C.M., J. Catal., 251, 2007, 97.
29. Chandrasekhar, S., Narsihmulu, Ch., Shameem Sultana, S., Ramakrishna Reddy, N., Org. Lett., 4, 2002, 4399.
30. Corma, A., Garcia, H., Leyva, A., J. Catal., 240, 2006, 87.
31. Beletskaya, I.P., Kashin, A.N., Litvinov, A.E., Tyurin, V.S., Valetsky, P.M., Van Koten, G., Organometallics, 25, 2006, 154.
32. Ribiere, P., Declerck, V., Nedellec, Y., Tetrahedron, 62, 2006, 10456.
33. Trzeciak, A.M., Mieczyńska, E., Ziółkowski, J.J., Bukowski, W., Bukowska, A., Noworól, J., Okal, J., New J. Chem., 32, 2008, 1124.
34. Zhang, L., Xue, M., Cui, Y., J. Appl. Polym. Sci., 115, 2010, 2523.
35. Bakherad, M., Keivanloo, A., Bahramian, B., Mihanparast, S., Tetrahedron Lett., 50, 2009, 6418.
36. Burguete, M.I., Garcia-Verdugo, E., Garcia-Villar, I., Gelat, F., Licence, P., Luis, S.V., Sans, V., J. Catal., 269, 2010, 150.
37. Diebold, C., Schweizer, S., Becht, J.-M., Le Drian, C., Org. Biomol. Chem., 8, 2010, 4834.
38. Demel, J., Sujandi, Park, S.-E., Čejka, J., Štěpnicka, P., J. Mol. Catal. A: Chem., 302, 2009, 28.
39. Byun, J.-W., Lee, Y.-S., Tetrahedron Lett., 45, 2004, 1837.
40. Caporusso, A.M., Innocenti, P., Aronica, L.A., Vitulli, G., Gallina, R., Biffis, A., Zecca, M., Corain, B., J. Catal., 234, 2005, 1.
41. Quignard, F., Choplin, A., Chem. Commun., 2001, 21.
42. Meier, M.A.R., Filali, M., Gohy, J.-F., Schubert, U.S., J. Mater. Chem., 16, 2006, 3001.
43. Schweizer, S., Becht, J.M., Le Drian, C., Tetrahedron, 66, 2010, 765.
44. Liu, G., Hou, M., Song, J., Jiang, T., Fan, H., Zhang, Z., Han, B., Green Chem., 12, 2010, 65.
45. Shin, J., Bertoia, J., Czerwinski, K.R., Bae, C., Green Chem., 11, 2009, 1576.
46. Ornelas, C., Diallo, A.K., Ruiz, J., Astruc, D., Adv. Synth. Catal., 351, 2009, 2147.
47. Islam, M., Mondal, P., Tuhina, K., Singha Roy, A., Mondal, S., Hossain, D., J. Organomet. Chem., 695, 2010, 2284.
48. Uozumi, Y., Matsuura, Y., Arakawa, T., Yamada, Y.M.A., Angew. Chem. Int. Ed., 48, 2009, 2708.
49. Li, J.-H., Hu, X.-Ch., Xie, Y.-X., Tetrahedron Lett., 47, 2006, 9239.
50. Alacid, E., Najera, C., J. Organomet. Chem., 694, 2009, 1658.
51. Schonfeldel, D., Nuyken, O., Weberskirch, R., J. Organomet. Chem., 690, 2005, 4648.
52. Narayanau, R., El-Sayed, M.A., J. Catal., 234, 2005, 348.
53. Narayanau, R., El-Sayed, M.A., J. Am. Chem. Soc., 125, 2003, 8340.
54. Gniewek, A., Ziółkowski, J.J., Trzeciak, A.M., Kępiński, L., J. Catal., 239, 2006, 272.
55. Duran Pachon, L., Rothenberg, G., Appl. Organomet. Chem., 22, 2008, 288.
56. Astruc, D., Lu, F., Aranzaes, J.R., Angew. Chem. Int. Ed., 44, 2005, 7852.
57. Durand, J., Teuma, E., Gomez, M., Eur. J. Inorg. Chem., 23, 2008, 3577.
58. Brayner, R., Viau, G., Bozon-Verduraz, F., J. Mol. Catal. A: Chem., 227, 2002, 182.
59. Evangelisti, C., Panziera, N., Pertici, P., Vitulli, G., Salvadori, P., Battocchio, C., Polzonetti, G., J. Catal., 262, 2009, 287.
60. Pathak, S., Greci, M.T., Kwong, R.C., Mercado, K., Surya Prakash, G.K., Olah, G.A., Thompson, M.E., Chem. Mater., 12, 2000, 1985.
61. Desforges, A., Backov, R., Deleuze, H., Montain-Monval, O., Adv. Funct. Mater., 15, 2005, 1689.
62. Yang, X., Fei, Z., Zhao, D., Han Ang, W., Li, Y., Dyson, P.J., Inorg. Chem., 47, 2008, 3292.
63. Borkowski, T., Trzeciak, A.M., Bukowski, W., Bukowska, A., Tylus, W., Kępiński, L., Appl. Catal. A: Gen., 378, 2010, 83.
64. Borkowski, T., Subik, P., Trzeciak, A.M., Wołowiec, S., Molecules, 16, 2011, 427.
65. Udayakumar, V., Alexander, S., Gayathri, V., Shivakumaraiah, Patil, K.R., Viswanathan, B., J. Mol. Catal. A: Chem., 317, 2010, 111.
66. Gurbuz, N., Ozdemir, I., Cetinkaya, B., Seckin, T., Appl. Organomet. Chem., 17, 2003, 776.
67. Szulmanowicz, M., Zawartka, W., Gniewek, A., Trzeciak, A.M., Inorg. Chim. Acta, 363, 2010, 4346.
68. Cypryk, M., Pospiech, P., Strzelec, K., Wąsikowska, K., Sobczak, J.W., J. Mol. Catal. A: Chem., 319, 2010, 30.
69. Cypryk, M., Pospiech, P., Strzelec, K., Sobczak, J.W., Phosphorus Sulfur Silicon Relat. Elem., 184, 2009, 1586.
70. Mizerska, U., Fortuniak, W., Chojnowski, J., Hałasa, R., Konopacka, A., Werel, W., Eur. Polym. J., 45, 2009, 779.
71. Franzen, R., Xu, Y., Can. J. Chem., 83, 2005, 266.
72. Leadbeater, N.E., M. Marco J. Org. Chem., 68, 2003, 888.
73. de Vries, J.G., Dalton Trans., 2006, 421.
74. Reetz, M.T., de Vries, J.G., Chem. Commun., 14, 2004, 1559.
75. Widegren, J.A., Bennett, M.A., Finke, R.G., J. Am. Chem. Soc., 125, 2003, 10301.
76. Hagen, C.M., Widegren, J.A., Maitlis, P.M., Finke, R.G., J. Am. Chem. Soc., 127, 2005, 4423.
77. Gniewek, A., Trzeciak, A.M., Ziółkowski, J.J., Kepiński, L., Wrzyszcz, J., Tylus, W., J. Catal., 229, 2005, 332.
78. Mathews, C.J., Smith, P.J., Welton, T., J. Mol. Catal. A: Chem., 206, 2003, 77.
79. Cotton, F.A., Inorg. Synth., 13, 1972, 52.