Monomeric metal aqua complexes in the interlayer space of montmorillonites as strong Lewis acid catalysts for heterogeneous carbon-carbon bond-forming reactions

Chemistry - A European Journal

Volumn 11, Issue 1, 2005, Pages 288-297

  Kawabata, Tomonori ^a   Kato, Masaki ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C bond formation; Heterogeneous catalysis; Lewis acid; Montmorillonite

Indexed keywords

COPPER NITRATE; DIELS-ALDER REACTIONS; MICHAEL REACTIONS; SCANDIUM TRIFLATE;

CATALYSTS; CHEMICAL BONDS; COPPER; ORGANIC SOLVENTS; POSITIVE IONS; REACTION KINETICS; SCANDIUM; SOLUTIONS;

COMPLEXATION;

CARBON; CARBONYL DERIVATIVE; COPPER ION; LEWIS ACID; METAL COMPLEX; MONOMER; MONTMORILLONITE; SCANDIUM; SODIUM ION;

ABSORPTION SPECTROSCOPY; ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIELS ALDER REACTION; EXTENDED X RAY ABSORPTION FINE STRUCTURE SPECTROSCOPY; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; MICHAEL ADDITION; SAKURAI HOSOMI ALLYLATION; XANES SPECTROSCOPY;

EID: 19944426398     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400672     Document Type: Article

References (93)

1. a) Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000;
2. b) Selectivities in Lewis Acid Promoted Reactions (Ed.: D. Schinzer), Kluwer Academic Publishers, Dordrecht, The Netherlands, 1989.
3. a) J. H. Clark, Green Chem. 1999, 1, 1;
4. b) P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, London, 1998.
5. J. H. Clark, Acc. Chem. Res. 2002, 35, 791.
6. For recent representative examples of supported Lewis acids for carbon-carbon bond forming reactions, see: Ag: a) C. Hague, N. J. Patmore, C. G. Frost, M. E Mahon, A. S. Weller, Chem. Commun. 2001, 2286;
7. Al: b) A, Díaz-Ortiz, A. de la Hoz, A. Moreno, A. Sánchez-Migallón, G. Valiente, Green Chem. 2002, 4, 339;
8. c) X. Hu, G. K. Chuah, S. Jaenicke, Appl. Catal. A 2001, 217, 1;
9. d) T. Nishimura, S. Ohtaka, A. Kimura, E. Hayama, Y. Haseba, H. Takeuchi, S. Uemura, Appl. Catal. A 2000, 194-195, 415;
10. B: e) Y. Qin, G. Cheng, A. Sundararaman, F. Jäkle, J. Am. Chem. Soc. 2002, 124, 12672;
11. Bi: f) B. M. Choudary, Ch. Sridhar, M. Sateesh, B. Sreedhar, J. Mol. Catal. A Chem. 2004, 212, 237;
12. Fe: g) B. M. Khadilkar, S. D. Bcirkar, Tetrahedron Lett. 1997, 38, 1641;
13. RE (rare earth): h) R Sreekanth, S.-W. Kim, T. Hyeon, B. M. Kim, Adv. Synth. Catal. 2003, 345, 936;
14. i) J. Perles, M. Iglesias, C. R. Valero, N. Snejko, Chem. Commun. 2003, 346;
15. j) W. Gu, W.-J. Zhou, D. L. Gin, Chem. Mater. 2001, 13, 1949;
16. k) M. T. Reetz, D. Giebel, Angew. Chem. 2000, 112, 2614; Angew. Chem. Int. Ed. 2000, 39, 2498;
17. k) M. T. Reetz, D. Giebel, Angew. Chem. 2000, 112, 2614; Angew. Chem. Int. Ed. 2000, 39, 2498;
18. l) S. Nagayama, S. Kobayashi, Angew. Chem. 2000, 112, 578; Angew. Chem. Int. Ed. 2000, 39, 567;
19. l) S. Nagayama, S. Kobayashi, Angew. Chem. 2000, 112, 578; Angew. Chem. Int. Ed. 2000, 39, 567;
20. m) R. Anwander, H. W. Görlitzer, G. Gerstberger, C. Palm, O. Runte, M. Spiegier, J. Chem. Soc. Dalton Trans. 1999, 3611;
21. n) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1998, 120, 2985;
22. o) H. Kotsuki, K. Arimura, Tetrahedron Lett. 1997, 38, 7583;
23. Sn: p) A. Corma, M. Renz, Chem. Commun. 2004, 550;
24. q) T. M. Jyothi, M. L. Kaliya, M. V. Landau, Angew. Chem. 2001, 113, 2965-2968; Angew. Chem. Int. Ed. 2001, 40, 2881-2884;
25. q) T. M. Jyothi, M. L. Kaliya, M. V. Landau, Angew. Chem. 2001, 113, 2965-2968; Angew. Chem. Int. Ed. 2001, 40, 2881-2884;
26. Zn: r) J. Liu, D. Yin, D. Yin, Z. Fut Q. Li, G. Lu, J. Mol. Catal. A Chem. 2004, 209, 171;
27. Zn/Fe: s) B. M. Khadilkar, S. D. Borkar, J. Chem. Technol. Biotechnol. 1998, 71, 209.
28. For reviews on solvent-free organic synthesis, see: a) G. W. V. Cave, C. L. Raston, J. L. Scott, Chem. Commun. 2001, 2159;
29. b) K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025;
30. c) J. O. Metzger, Angew. Chem. 1998, 110, 3145; Angew. Chem. Int. Ed. 1998, 37, 2975;
31. c) J. O. Metzger, Angew. Chem. 1998, 110, 3145; Angew. Chem. Int. Ed. 1998, 37, 2975;
32. a) Organic Syntheis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
33. C-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997.
34. a) P. Laszlo, Science 1987, 235, 1473;
35. b) T. J. Pinnavaia, Science 1983, 220, 365.
36. Excellent reviews of mont-catalyzed organic syntheses: a) J. H. Clark, D. J. Macquarrie, Chem. Soc. Rev. 1996, 25, 303;
37. b) Y. Izumi, M. Onaka, Adv. Catal. 1992, 38, 245;
38. c) P. Laszlo, Acc. Chem. Res. 1986, 19, 121.
39. Ti: a) T. Kawabata, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2003, 44, 9205;
40. b) T. Kawabata, M. Kato, T. Mizugaki, K. Ebitani, K. Kaneda, Chem. Lett. 2003, 32, 648;
41. c) T. Kawabata, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett. 2001, 42, 8329;
42. d) K. Ebitani, T. Kawabata, K. Nagashima, T. Mizugaki, K. Kaneda, Green Chem. 2000, 2, 157;
43. Fe: e) K. Ebitani, M. Ide, T. Mitsudome, T. Mizugaki, K. Kaneda, Chem. Commun. 2002, 690;
44. Sc: f) T. Kawabata, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2003, 125, 10 486.
45. K. Ebitani, K. Nagashima, T. Mizugaki, K. Kaneda, Chem. Commun. 2000, 869.
46. G. F. McCann, G. J. Millar, G. A. Bowmaker, R. P. Cooney, J. Chem. Soc. Faraday Trans. 1995, 91, 4321.
47. a) T. Yamamoto, T. Tanaka, R. Kuma, S. Suzuki, F. Amano, Y. Shimooka, Y. Kohno, T. Funabiki, S. Yoshida, Phys. Chem. Chem. Phys. 2002, 4, 2449;
48. b) L.-S. Kau, D. J. Spira-Solomon, J. E. Penner-Harn, K. O. Hodgson, E. I. Solomon, J. Am. Chem. Soc. 1987, 109, 6433.
49. F. A. Cotton, G Wilkinson, Advanced Inorganic Chemistry, 5th ed., Wiley, New York, 1988, p. 755.
50. C. Lamberti, G. Spoto, D. Scarano, C. Pazé, M. Salvalaggio, S. Bordiga, A. Zecchina, G. T. Palomino, F. D'Acapito, Chem. Phys. Lett. 1997, 269, 500.
51. H. Ohtaki, M. Maeda, Bull. Chem. Soc. Jpn. 1974, 47, 2197.
52. M. B. McBride, T. J. Pinnavaia, M. M. Mortland, J. Phys. Chem. 1975, 79, 2430.
53. J. M. Harrowfield, B. W. Skelton, A. H. White, Aust. J. Chem. 1994, 47, 397.
54. Y. Ohni, Y Suzuki, T. Takeguchi, A. Ouchi, Bull. Chem. Soc. Jpn. 1988, 61, 393.
55. G. R. Willey, P. R. Meehan, M. D. Rudd, M. G. B. Drew, J. Chem. Soc. Dalton Trans. 1995, 3175.
56. S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287.
57. a) T.-L. Ho, Tactics of Organic Synthesis, Wiley, New York, 1994;
58. b) M. E. Jung in Comprehensive Organic Synthesis, Vol. 4, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p.1;
59. c) H. O. House, Modern Synthetic Reactions, 2nd ed., Benjamin, Menlo Park, Calif., 1972, p. 595;
60. d) For an excellent review on transition-metalcatalyzed Michael reaction of 1,3-dicarbonyl compounds, see: J. Christoffers, Eur. J. Org. Chem. 1998, 1259.
61. 2O.
62. zz values of ESR spectra of Superoxide metal ion complexes (Sc 1.00; Y 0.85; Yb 0.83; La 0.82; Zn 0.71; Na 0.34). See: a) S. Fukuzumi, K. Ohkubo, J. Am. Chem. Soc. 2002, 124, 10270;
63. b) S. Fukuzumi, K. Ohkubo, Chem. Eur. J. 2000, 6, 4532.
64. J. Christoffers, Chem. Commun. 1997, 943.
65. A. C. Coda, G. Desimoni, P. Righetti, G. Tacconi, Gazz. Chim. Ital. 1984, 114, 417.
66. S. Matsunaga, T. Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3, and references therein.
67. K. Mori, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2003, 725, 11460.
68. C. F. Baes, Jr., R. Mesmer, The Hydrolysis of Cations, Wiley, New York, 1976.
69. S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 702, 2227.
70. For a review see: S. Kobayashi, Eur. J. Org. Chem. 1999, 15.
71. S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209.
72. S. Kobayashi, I. Hachiya, J. Org. Chem. 1994, 59, 3590.
73. M. Onaka, Yuki Gosei Kagaku Kyokaishi 1995, 53, 392.
74. Y. Mon, K. Kakumoto, K. Manabe, S. Kobayashi, Tetrahedron Lett. 2000, 41, 3107.
75. a) J. A. Marshall, Chem. Rev. 1996, 96, 31;
76. b) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207;
77. c) A. Hosomi, Acc. Chem. Res. 1988, 21, 200.
78. [9a-d] can be used in the absence of ethanol for the desilylation to homoallylic alcohols even at 50°C.
79. A. Marx, H. Yamamoto, Angew. Chem. 2000, 112, 182; Angew. Chem. Int. Ed. 2000, 39, 178;
80. A. Marx, H. Yamamoto, Angew. Chem. 2000, 112, 182; Angew. Chem. Int. Ed. 2000, 39, 178;
81. X. Fang, J. G. Watkin, B. P. Warner, Tetrahedron Lett. 2000, 41, 447.
82. M. W. Wang, Y. J. Chen, D. Wang, Synlett 2000, 385.
83. Y. Onishi, T. Ito, M. Yasuda, A. Baba, Eur. J. Org. Chem. 2002, 1578.
84. M. Kawai, M. Onaka, Y. Izumi, Chem. Lett. 1986, 381.
85. a) A. Corma, L. T. Nemeth, M. Renz, S. Valencia, Nature 2001, 412, 423;
86. b) A. Corma, M. E. Domine, L. Nemeth, S. Valencia, J. Am. Chem. Soc. 2002, 124, 3194.
87. a) J. W. Carmichael, Jr., L. K. Steinrauf, R. L. Belford, J. Chem. Phys. 1965, 43, 3959;
88. b) K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., pt. B, Wiley, New York, 1997, p. 91.
89. J. Christoffers, Chem. Eur. J. 2003, 9, 4862.
90. 3+-mont (8.3 Å).
91. Purification of Laboratory Chemicals, 3rd ed. (Eds.: D.D. Perrin, W. L. F. Armarego), Pergamon, Oxford, 1988.
92. M. Kökerling, G. Geismar, G. Henkel, and H.-F. Nolting, J. Chem. Soc. Faraday Trans. 1997, 93, 481.
93. T. Tanaka, H. Yamashita, R. Tsuchitani, T. Funabiki, S. Yoshida, J. Chem. Soc. Faraday Trans. 1988, 84, 2987.