Synthesis and catalytic evaluation in the Heck reaction of deposited palladium catalysts immobilized via amide linkers and their molecular analogues

Catalysis Today

Volumn 227, Issue , 2014, Pages 207-214

  Semler, Miloslav ^a,b   Čejka, Jiří ^b   Štěpnička, Petr ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

Amide linkers; Deposited catalysts; Heck reaction; Palladium; Poisoning tests

Indexed keywords

CATALYTIC EVALUATION; HECK REACTIONS; HETEROGENIZED CATALYSTS; MOLECULAR ANALOGUES; N-BUTYL ACRYLATE; PALLADIUM ACETATE; PALLADIUM CATALYST; RESULTING MATERIALS;

AMIDES; METALS; PALLADIUM; PALLADIUM COMPOUNDS; SILICA GEL; SYNTHESIS (CHEMICAL); VOLATILE FATTY ACIDS;

CATALYST POISONING;

EID: 84900377061     PISSN: 09205861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cattod.2013.09.012     Document Type: Article

References (56)

1. R.F. Heck, and J.P. Nolley J. Org. Chem. 37 1972 2320 2322
2. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581
3. I.P. Belestskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
4. S. de Brase, and A. Meijere F. Diederich, P.J. Stang, Metal-catalyzed Cross-coupling Reactions 1998 Wiley-VCH New York 99 166
5. J.T. Link, and L.E. Overman F. Diederich, P.J. Stang, Metal-catalyzed Cross-coupling Reactions 1998 Wiley-VCH New York 231 269
6. W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2 7
7. A. de Meijere, and F.E. Meyer Angew. Chem. Int. Ed. Engl. 33 1994 2379 2411
8. S.E. Gibson, and R.J. Middleton Contemp. Org. Synth. 3 1996 447 471
9. M. Shibasaki, C.D.J. Boden, and A. Kojima Tetrahedron 53 1997 7371 7393
10. J.G. de Vries Can. J. Chem. 79 2001 1086 1092
11. C.E. Tucker, and J.G. de Vries Top. Catal. 19 2002 111 118
12. C. Torborg, and M. Beller Adv. Synth. Catal. 351 2009 3027 3043 and references cited therein
13. M. Pagliaro, V. Pandarus, R. Ciriminna, F. Béland, and P.D. Carà ChemCatChem 4 2012 432 445
14. European Medicines Agency document no. CPMP/SWP/QWP/4446/00 corrigendum of February 2008 available at http://www.ema.europa.eu/ema/pages/includes/ document/open-document.jsp?webContentId=WC500003586 (retrieved on June 10, 2013).
15. J. Demel, S.-E. Sujandi, J. Park, P. Čejka, and Štěpnička J. Mol. Catal. A: Chem. 302 2009 28 35
16. J. Demel, M. Lamač, J. Čejka, and P. Ště pnička ChemSusChem 2 2009 442 451
17. J. Demel, J. Čejka, and P. Štěpnička J. Mol. Catal. A: Chem. 329 2010 13 20
18. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, and J.S. Beck Nature 359 1992 710 712
19. J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins, and J.L. Schlenker J. Am. Chem. Soc. 114 1992 10834 10843
20. B. Zhao, Q. Huo, J. Feng, B.F. Chmelka, and G.D. Stucky J. Am. Chem. Soc. 120 1998 6024 6036
21. S.F. Zhao, R.X. Zhou, and X.M. Zheng J. Mol. Catal. A: Chem. 211 2004 139 142
22. J. Zhou, R. Zhou, L. Mo, S. Zhao, and X. Zheng J. Mol. Catal. A: Chem. 178 2002 289 292
23. S. Mandal, D. Roy, R.V. Chaudhari, and M. Sastry Chem. Mater. 16 2004 3714 3724
24. P. Veerakumar, M. Velayudham, K.-L. Lu, and S. Rajagopal Appl. Catal. A: Gen. 455 2013 247 260
25. S. Ungureanu, H. Deleuze, O. Babot, M.-F. Achard, C. Sanchez, M.I. Popa, and R. Backov Appl. Catal. A: Gen. 390 2010 51 58
26. H. Li, L. Wang, and P. Li Synthesis 2007 1635 1642
27. P. Wang, Q. Lu, and J. Li Mater. Res. Bull. 45 2010 129 134
28. S. Martinez, M. Moreno-Manas, A. Allribera, U. Schubert, A. Roig, and E. Molins New J. Chem. 30 2006 1093 1097
29. V. Purcar, D. Donescu, C. Petcu, R. Luque, and D.J. Macquarie Catal. Commun. 10 2009 395 400
30. K.-I. Schimizu, S. Koizumi, T. Hatamachi, H. Yoshida, S. Komai, T. Kodama, and Y. Kitayama J. Catal. 228 2004 141 151
31. C.M. Crudden, M. Sateesh, and R. Lewis J. Am. Chem. Soc. 127 2005 10045 10050
32. J.M. Richardson, and C.W. Jones J. Catal. 251 2007 80 93
33. Q. Xu, and M. Cai React. Funct. Polym. 67 2007 515 521
34. R.-X. Zhou, J.-M. Zhou, and X.-M. Zheng React. Kinet. Catal. Lett. 87 2006 157 163
35. G. Martra, L. Bertinetti, C. Gerbaldi, R. Maggi, G. Sartori, and S. Coluccia Catal. Lett. 132 2009 50 57 and ref. [8e]
36. R. Chanthateyanonth, and H. Alper J. Mol. Catal. A: Chem. 201 2003 23 31
37. M. Cai, and J. Sha Catal. Commun. 8 2007 1691 1696
38. G. Singh, S. Bali, and A.K. Singh Polyhedron 26 2007 897 903
39. Q. Hu, J.E. Hampsey, N. Jiang, C. Li, and Y. Lu Chem. Mater. 17 2005 1561 1569
40. P. Yi, Z. Zhuangyu, and H. Hongwen J. Mol. Catal. 62 1990 297 306
41. S. Tandukar, and A. Sen J. Mol. Catal. A: Chem. 268 2007 112 119
42. H. Yang, X. Han, G. Li, and Y. Wang Green Chem. 11 2009 1184 1193
43. B. Karimi, and D. Enders Org. Lett. 8 2006 1237 1240
44. J.-Y. Jung, A. Taher, H.-J. Kim, W.-S. Ahn, and M.-J. Jin Synlett 2009 39 42
45. N. Gurbuz, I. Özdemir, B. Cetinkaya, and T. Seckin Appl. Organomet. Chem. 17 2003 776 780
46. E. Tyrrell, L. Whiteman, and N. Williams J. Organomet. Chem. 696 2011 3472 3645
47. N. Brun, P. Hesemann, G. Laurent, C. Sanchez, M. Birot, H. Deleuze, and R. Backov New J. Chem. 35 2013 157 168
48. R. Sayah, K. Glegola, E. Framery, and V. Dufaud Adv. Synth. Catal. 349 2007 373 381
49. B. Karimi, S. Abedi, J.H. Clark, and V. Budarin Angew. Chem. Int. Ed. 45 2006 4776 4779
50. A. El-Faham, and F. Albericio Chem. Rev. 111 2011 6557 6602
51. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606 631
52. Y. Borodko, J.W. Ager III, G.E. Marti, H. Song, K. Niesz, and G.A. Samorjai J. Phys. Chem. B 109 2005 17386 17390
53. S.M. Chemtob, G.R. Rossman, and J.F. Stebbins Am. Mineral. 97 2012 203 211
54. Y. Coquerel, P. Brémond, and J. Rodriguez J. Organomet. Chem. 692 2007 4805 4808
55. J.A. Widegren, and R.G. Finke J. Mol. Catal. A: Chem. 198 2003 317 341
56. T. Jarolím, and J. Podlahová J. Inorg. Nucl. Chem. 38 1976 125 129