Heck coupling by Pd deposited onto organic-inorganic hybrid supports

Journal of Molecular Catalysis A: Chemical

Volumn 229, Issue 1-2, 2005, Pages 107-116

  Papp, Attila ^a   Miklós, Krisztina ^a   Forgo, Péter ^a   Molnár, Árpád ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

C C coupling; Heterogeneous catalysis; Leaching; Palladium; Surface effect

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHEMICAL MODIFICATION; CHEMISORPTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; RECYCLING; REDUCTION; SILANES; SILICA; TRANSMISSION ELECTRON MICROSCOPY;

CHLOROORGANOHYDROSILANES; FUNCTIONAL AROMATIC GROUPS; HECK COUPLING; HETEROGENEOUS CATALYSTS;

CATALYSTS;

INORGANIC COMPOUND; ORGANIC COMPOUND; PALLADIUM; SILICON DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; HECK COUPLING; LEACHING; REDUCTION; SYNTHESIS;

EID: 13444267563     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.11.011     Document Type: Article

References (92)

1. R.F. Heck, and J.P. Nolley Jr. J. Org. Chem. 37 1972 2320
2. R.F. Heck Acc. Chem. Res. 12 1979 146 151
3. A. de Meijere, and F.E. Meyer Angew. Chem. Int. Ed. 33 1994 2379
4. W.A. Herrmann B. Cornils W.A. Herrmann Applied Homogeneous Catalysis with Organometallic Compounds 1996 VCH Weinhem 712
5. S. Bräse, and S.A. de Meijere F. Diederich P.J. Stang Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim 99 (Chapter 3)
6. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
7. A. Eisenstadt, and D.J. Ager R.A. Sheldon H. van Bekkum Fine Chemicals through Heterogeneous Catalysis 2001 Wiley-VCH Weinheim 576
8. A. Zapf, and M. Beller Topics Catal. 19 2002 101
9. C.E. Tucker, and J.G. de Vries Topics Catal. 19 2002 111
10. N.J. Whitcombe, K.K. Hii, and S.E. Gibson Tetrahedron 57 2001 7449
11. D.S. McGuinness, K.J. Cavell, B.W. Skelton, and A.H. White Organometallics 18 1999 1596
12. Y. Ikeda, T. Nakamura, H. Yorimitsu, and K. Oshima J. Am. Chem. Soc. 124 2002 6514
13. Y. Na, S. Park, S.B. Han, H. Han, S. Ko, and S. Chang J. Am. Chem. Soc. 126 2004 250
14. M.T. Reetz, E. Westerman, R. Lohmer, and G. Lohmer Tetrahedron Lett. 39 1998 8449
15. A.J. Carmichael, M.J. Earle, J.D. Holbrey, P.B. McCormac, and K.R. Seddon Org. Lett. 1 1999 997
16. K.S.A. Vallin, P. Emilsson, M. Larhed, and A. Hallberg J. Org. Chem. 67 2002 6243
17. S. Chrasekhar, Ch. Narsihmulu, S.S. Sultana, and N.R. Reddy Org. Lett. 4 2002 4399
18. Q. Yao, E.P. Kinney, and Z. Yang J. Org. Chem. 68 2003 7528
19. A.H.M. de Vries, F.J. Parlevliet, L. Schmieder-van de Vondervoort, J.H.M. Mommers, H.J.W. Henderickx, M.A.M. Walet, and J.G. de Vries Adv. Synth. Catal. 344 2002 996
20. A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285
21. A.F. Littke, and G.C. Fu Angew. Chem. Int. Ed. 41 2002 4176
22. R.B. Bedford Chem. Commun. 2003 1787
23. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23
24. K.H. Shaughnessy, P. Kim, and J.F. Hartwig J. Am. Chem. Soc. 121 1999 2123
25. D. Morales-Morales, R. Redón, C. Yung, and C.M. Jensen Chem. Commun. 2000 1619
26. A. Ehrentraut, A. Zapf, and M. Beller Synlett 2000 1589
27. A.F. Littke, and G.C. Fu J. Am. Chem. Soc. 123 2001 6989
28. A. Schnyder, A.F. Indolese, M. Studer, and H.U. Blaser Angew. Chem. Int. Ed. 41 2002 3668
29. I.D. Kostas, B.R. Steele, A. Terzis, and S.V. Amosova Tetrahedron 59 2003 3467
30. C.-A. Lin, and F.-T. Luo Tetrahedron Lett. 44 2003 7565
31. C. Wolf, and R. Lerebours J. Org. Chem. 68 2003 7077
32. C.S. Consorti, M.L. Zanini, S. Leal, G. Ebeling, and J. Dupont Org. Lett. 5 2003 983
33. C. Nájera, J. Gil-Moltó, S. Karlström, and L.R. Falvello Org. Lett. 5 2003 1451
34. I.G. Jung, S.U. Son, K.H. Park, K.-C. Chung, J.W. Lee, and Y.K. Chung Organometallics 22 2003 4715
35. V.P.W. Böhm, and W.A. Herrmann Chem. Eur. J. 6 2000 1017
36. K. Selvakumar, A. Zapf, and M. Beller M. Org. Lett. 4 2002 3031
37. S.B. Park, and H. Alper Org. Lett. 5 2003 3209
38. M.R. Buchmeiser, T. Schareina, R. Kempe, and K. Wurst J. Organomet. Chem. 634 2001 9
39. A. Dahan, and M. Portnoy Org. Lett. 5 2003 1197
40. A. Datta, K. Ebert, and J. Plenio Organometallics 22 2003 4685
41. J. Schwarz, V.P.W. Böhm, M.G. Gardiner, M. Grosche, W.A. Herrmann, W. Hieringer, and G. Raudaschl-Sieber Chem. Eur. J. 6 2000 1773
42. J.H. Clark, J. Macquarrie, and E.B. Mubofu Green Chem. 2 2000 53
43. J. Zhou, R. Zhou, L. Mo, S. Zhao, and X. Zheng J. Mol. Catal. A: Chem. 178 2002 289
44. M. Lagasi, and P. Moggi J. Mol. Catal. A: Chem. 182-183 2002 61
45. B.M. Choudary, M.L. Kantam, N.M. Reddy, and N.M. Gupta Catal. Lett. 82 2002 79
46. R.K. Ramachani, B.S. Uphade, M.P. Vinod, R.D. Wakharkar, V.R. Choudhary, and A. Sudalai Chem. Commun. 1997 2071
47. L. Djakovitch, and K. Koehler J. Am. Chem. Soc. 123 2001 5990
48. M. Dams, L. Drijkoningen, B. Pauwels, G. Van Tendeloo, D.E. De Vos, and P.A. Jacobs J. Catal. 209 2002 225
49. T.H. Bennur, A. Ramani, R. Bal, B.M. Cha, and S. Sivasanaker Catal. Commun. 3 2002 493
50. A. Corma, H. García, A. Leyva, and A. Primo Appl. Catal. A 247 2003 41
51. A. Corma, H. García, A. Leyva, and A. Primo Appl. Catal. A 257 2004 77
52. M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, and W.A. Herrmann J. Organomet. Chem. 520 1996 257
53. J. Le Bars, U. Specht, J.S. Bradley, and D.G. Blackmond Langmuir 15 1999 7621
54. M.T. Reetz, and G. Lohmer Chem. Commun. 1996 1921
55. M.T. Reetz, and E. Westermann Angew. Chem. Int. Ed. 39 2000 165
56. A. Biffis, M. Zecca, and M. Basato J. Mol. Catal. A: Chem. 173 2001 249
57. M. Moreno-Mañas, R. Pleixats, and S. Villarroya Organometallics 20 2001 4524
58. C. Rocaboy, and J.A. Gladysz Org. Lett. 4 2002 1993
59. V. Caló, A. Nacci, A. Monopoli, S. Laera, and N. Cioffi J. Org. Chem. 68 2003 2929
60. V. Caló, A. Nacci, A. Monopoli, A. Detomaso, and P. Iliade Organometallics 22 2003 4193
61. B.M. Bhanage, and M. Arai Catal. Rev. -Sci. Eng. 43 2001 315
62. A. Eisenstadt F. Herkes Catalysis of Organic Reactions 1998 Marcel Dekker New York 415
63. F.Y. Zhao, B.M. Bhanage, M. Shirai, and M. Arai Chem. Eur. J. 6 2000 843
64. F.Y. Zhao, M. Shirai, Y. Ikushima, and M. Arai J. Mol. Catal. A: Chem. 180 2002 211
65. K. Köhler, R.G. Heidenreich, J.G.E. Krauter, and J. Pietsch Chem. Eur. J. 8 2002 622
66. R.G. Heidenreich, J.G.E. Krauter, J. Pietsch, and K. Köhler J. Mol. Catal. A: Chem. 182-183 2002 499
67. R.G. Heidenreich, K. Köhler, J.G.E. Krauter, and J. Pietsch Synlett 2002 1118
68. C.P. Mehnert, and J.Y. Ying Chem. Commun. 1997 2215
69. C.P. Mehnert, D.W. Weaver, and J.Y. Ying J. Am. Chem. Soc. 120 1998 12289
70. L. Djakovitch, and K. Koehler J. Mol. Catal. A: Chem. 142 1999 275
71. K. Köhler, M. Wagner, and L. Djakovitch Catal. Today 66 2001 105
72. R. Srivastava, N. Venkatathri, D. Srinivas, and P. Ratnasamy Tetrahedron Lett. 44 2003 3649
73. S.B. Waghmode, S.G. Wagholikar, and S. Sivasanker Bull. Chem. Soc. Jpn. 76 2003 1989
74. M. Wagner, K. Köhler, L. Djakovitch, S. Weinkauf, V. Hagen, and M. Muhler Topics Catal. 13 2000 319
75. B.M. Choudary, S. Madhi, N.S. Chowdari, M.L. Kantam, and B. Sreedhar J. Am. Chem. Soc. 124 2002 14127
76. Y. Mori, and M. Seki J. Org. Chem. 68 2003 1571
77. S. Iyer, and V.V. Thakur J. Mol. Catal. A: Chem. 157 2000 275
78. S.S. Pröckl, W. Kleist, M.A. Gruber, and K. Köhler Angew. Chem. Int. Ed. 43 2004 1881
79. M.T. Reetz, and J.G. de Vries Chem. Commun. 2004 1559
80. Á. Molnár, A. Papp, K. Miklós, and P. Forgo Chem. Commun. 2003 2626
81. D.V. Nadkarni, and J.L. Fry J. Chem. Soc., Chem. Commun. 1993 997
82. J.J. Reed-Mundell, D.V. Nadkarni, J.M. Kunz Jr., C.W. Fry, and J.L. Fry Chem. Mater. 7 1995 1655
83. D.W. Sindorf, and G.E. Maciel J. Am. Chem. Soc. 105 1983 3767
84. E.F. Vansant, P. Van Dr Voort, and K.C. Vrancken Characterization and Chemical Modification of the Silica Surface 1997 Elsevier Amsterdam (Chapter 9)
85. C.-M. Andersson, and A. Hallberg J. Org. Chem. 52 1987 3529
86. W. Cabri, I. Candiani, and A. Bedeschi J. Org. Chem. 55 1990 3654
87. W. Cabri, I. Candiani, A. Bedeschi, and R. Santi J. Org. Chem. 57 1992 3558
88. L. Djakovitch, H. Heise, and K. Köhler J. Organomet. Chem. 584 1999 16
89. A. Biffis, M. Zecca, and M. Basato Eur. J. Inorg. Chem. 2001 1131
90. J.A. Widegren, and R.G. Finke J. Mol. Catal. A: Chem. 198 2003 317
91. F.Y. Zhao, M. Shirai, and M. Arai J. Mol. Catal. A: Chem. 154 2000 39
92. F.Y. Zhao, M. Shirai, and M. Arai J. Catal. 194 2000 479