Soluble gold and palladium complexes heterogenized on MCM-41 are effective and versatile catalysts

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2008, Pages 1107-1115

  González Arellano, Camino ^a,b   Corma, Avelino ^c   Iglesias, Marta ^a   Sánchez, Félix ^b  

^a INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c CSIC   (Spain)

Author keywords

C C coupling; Gold; Hydrogenation; Palladium; Schiff bases; Supported catalysts

Indexed keywords

CATALYST ACTIVITY; GOLD COMPOUNDS; HYDROGENATION; MESOPOROUS MATERIALS; PALLADIUM COMPOUNDS; SILICA;

C-C COUPLING; CATALYSE; CHIRAL SCHIFF-BASE; GOLD; GOLD COMPLEXES; IMMOBILIZED CATALYSTS; ORDERED MESOPOROUS SILICAS; PALLADIUM COMPLEXES; SCHIFF-BASE; ]+ CATALYST;

CATALYST SUPPORTS;

EID: 53349165241     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700955     Document Type: Article

References (75)

1. a) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
2. b) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896;
3. c) G. C. Bond, C. Louis, D. T. Thompson in Catalysis by Gold, Imperial College Press, London, 2006;
4. d) G. Dyker, Angew. Chem. Int. Ed. 2000, 39, 4237 and references cited therein.
5. A. Corma, H. García, Chem. Rev. 2003, 103, 4307.
6. a) X. Yao, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 6884;
7. b) C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 9584.
8. a) M. Haruta, N. Yamada, T. Kobayashi, S. Iijima, J. Catal. 1989, 115, 301;
9. b) J. Guzman, B. C. Gates, J. Am. Chem. Soc. 2004, 126, 2672;
10. c) M. C. Daniel, D. Astruc, Chem. Rev. 2004, 104, 293;
11. d) C. Lemire, R. Meyer, S. Shaikhutdinov, H. J. Freund, Angew. Chem. Int. Ed. 2004, 43, 118.
12. A. Corma, P. Serna, Science 2006, 313, 332.
13. a) L. Prati, M. Rossi, J. Catal. 1998, 176, 552;
14. b) A. Abad, P. Concepción, A. Corma, H. García, Angew. Chem. Int. Ed. 2005, 44, 4066;
15. c) D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F. Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight, G. J. Hutchings, Science 2006, 311, 362.
16. a) S. Carrettin, J. Guzmán, A. Corma, Angew. Chem. Int. Ed. 2005, 44, 2242;
17. b) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. Int. Ed. 2000, 39, 2285.
18. a) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2005, 44, 6990;
19. b) A. Arcadi, S. Di Giuseppe, Curr. Org. Chem. 2004, 8, 795;
20. c) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387;
21. d) A. S. K. Hashmi, Gold Bull. 2003, 36, 3;
22. e) A.S.K. Hashmi, Gold Bull. 2004, 37, 51;
23. f) C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 3451;
24. g) A. S. K. Hashmi, R. Salatte, W. Frey, Chem. Eur. J. 2006, 12, 6991;
25. h) A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. Int. Ed. 2004, 43, 6545.
26. a) H. U. Blaser, Tetrahedron: Asymmetry 1991, 2, 843;
27. b) R. Noyori in Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
28. c) I. Ojima, in Catalytic Asymmetric Synthesis, 2nd ed., Wiley-VCH, New York, 2000;
29. d) E. N. Jacobsen, A. Pfaltz, H. Yamamoto in Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999.
30. a) C. U. Pittman Jr. in Comprehensive Organometallic Chemistry (Ed.: G. Wilkinson), Pergamon, Oxford, 1992, vol. 8, p. 553;
31. b) S. C. Bourque, H. Alper, L. E. Manzer, P. Arya, J. Am. Chem. Soc. 2000, 122, 956.
32. a) D. E. Vos, I. F. K. Vankelecom, P. A. Jacobs in Chiral Catalyst Immobilisation and Recycling, Wiley-VCH, Weinheim, 2000;
33. b) J. M. Thomas, R. Raja, D. W. Lewis, Angew. Chem. Int. Ed. 2005, 44, 6456;
34. c) M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. Int. Ed. 2006, 45, 4732;
35. d) R. Augustine, S. Tanielyan, S. Anderson, H. Yang, Chem. Commun. 1999, 1257;
36. e) C. Bianchini, D. G. Burnaby, J. Evans, P. Frediani, A. Meli, W. Oberhauser, R. Psaro, L. Sordelli, F. Vizza, J. Am. Chem. Soc. 1999, 121, 5961;
37. f) H.-B. Yu, Q.-S. G. Hu, L. Pu, Tetrahedron Lett. 2000, 41, 1681;
38. g) H. Gao, R. Angelici, J. Mol. Catal. A 1999, 149, 63;
39. h) K. Nozaki, Y. Itoi, F. Shibahara, E. Shirakawa, T. Ohta, H. Takaya, T. Hiyama, J. Am. Chem. Soc. 1998, 120, 4051.
40. D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489 and references cited therein.
41. C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 1990.
42. a) C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, J. Catal. 2006, 238, 497-501;
43. b) C. González-Arellano, A. Abad, A. Corma, H. García, M. Iglesias, F. Sánchez, Angew. Chem. Int. Ed. 2007, 46, 1536-1538.
44. A. Corma, E. Gutiérrez-Puebla, M. Iglesias, A. Monge, S. Pérez-Ferreras, F. Sánchez, Adv. Synth. Catal. 2006, 348, 1899.
45. C. González-Arellano, E. Gutiérrez-Puebla, M. Iglesias, F. Sánchez, Eur. J. Inorg. Chem. 2004, 1955.
46. a) A. Corma, C. del Pino, M. Iglesias, F. Sánchez, J. Chem. Soc., Chem. Commun. 1991, 1253;
47. b) A. Corma, M. Iglesias, M. V. Martín, J. Rubio, F. Sánchez, Tetrahedron: Asymmetry 1992, 3, 845;
48. c) A. Corma, A. Fuerte, M. Iglesias, F. Sánchez, J. Mol. Catal. A 1996, 107, 225 and references cited therein;
49. d) M. J. Alcón, A. Corma, M. Iglesias, F. Sánchez, J. Mol. Catal. A 2003, 194, 137.
50. C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Adv. Synth. Catal. 2004, 346, 1316.
51. a) H. Onoue, I. Moritani, J. Organomet. Chem. 1972, 43, 431;
52. b) H. Onoue, K. Minami, K. Nakagawa, Bull. Chem. Soc. Jpn. 1970, 43, 3480.
53. K. Nakamoto, IR and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., J. Wiley & Sons, New York, 1997.
54. T. N. Sorrell, W. E. Allen, P. S. White, Inorg. Chem. 1995, 34, 952.
55. A. B. P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, 1984.
56. a) C. A. Brown, V. K. Ahuja, J. Org. Chem. 1973, 38, 2226;
57. b) D. R. Anton, R. Crabtree, Organometallics 1983, 2, 855.
58. A. Comas-Vives, C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, G. Ujaque, J. Am. Chem. Soc. 2006, 128, 4756.
59. a) T. Mirizoki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581;
60. b) V. Farina, Adv. Synth. Catal. 2004, 346, 1553.
61. a) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513;
62. b) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419.
63. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
64. b) P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 2000, 39, 2633.
65. a) Metal-Catalysed Cross-Coupling Reactions (Eds.: F. Diederich, P. G. Stang), Wiley-VCH, Weinheim, 1997;
66. b) Transition Metals for Organic Synthesis; Building Blocks and Fine Chemicals (Ed.: M. Beller), Wiley-VCH, Weinheim, 2004.
67. N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458.
68. a) B. M. Bhanage, F. G. Zhao, M. Shirai, M. Arai, Tetrahedron Lett. 1998, 39, 9509;
69. b) B. M. Bhanage, S.-I. Fujita, M. Arai, J. Organomet. Chem. 2003, 687, 211;
70. c) C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Adv. Synth. Catal. 2004, 346, 1758.
71. a) W. M. H. Sachtler, Acc. Chem. Res. 1993, 26, 383;
72. b) D. Brunel, N. Bellocq, P. Sutra, Coord. Chem. Rev. 1998, 178, 1085.
73. Due to the similarity of the spectra for the supported catalysts in each series of ligands, only the data for some compounds are given. Data for all compounds are given as Supporting Information.
74. a) J. S. Beck, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T.-W. Chu, K. H. Olson, E. Sheppard, S. B. McCullen, J. B. Higgins, J. L. Schlenk, J. Am. Chem. Soc. 1992, 114, 10834.
75. C.-W. Ho, W.-C. Cheng, M.-C. Cheng, S.-M. Peng, K.-F. Cheng, C.-M. Che, J. Chem. Soc., Dalton Trans. 1996, 405.