A polymer-supported scandium catalyst

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2256-2257

  Kobayashi, Shu ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001017480     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960003n     Document Type: Article

References (37)

1. Reviews: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. (c) Frechet, J. M. J. Tetrahedron 1981, 37, 663.
2. Reviews: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. (c) Frechet, J. M. J. Tetrahedron 1981, 37, 663.
3. Reviews: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Akelah, A.; Sherrington, D. C. Ibid. 1981, 81, 557. (c) Frechet, J. M. J. Tetrahedron 1981, 37, 663.
4. Recently, Lewis acid-mediated reactions have been especially focused upon because of their unique reactivities, selectivities, and mild conditions. Schinzer, D., Ed. Selectivities in Lewis Acid Promoted Reactions; Kluwer Academic Publishers: Dordrecht, 1989
5. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
6. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
7. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
8. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
9. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
10. 3 onto polymers or inorganic support materials has been reported, but the successful applications have been limited, (a) Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem. Soc. 1972, 94, 9284. (b) Krzywicki, A.; Marczewski, M. J. Chem. Soc., Faraday Trans 1 1980, 1311. (c) Drago, R. S.; Getty, E. E. J. Am. Chem. Soc. 1988, 110, 3311. (d) Clark, J. H.; Martin, K.; Teasdale, A. J.; Barlow, S. J. J. Chem. Soc., Chem. Commun. 1995, 2037. Montmorillomte-supported zinc chloride: (e) Clark, J. H.; Cullen, S. R.; Barlow, S. J ; Bastock, T. W. J. Chem. Soc., Perkin Trans. 2 1994, 1117. Immobilized trityl salts: (f) Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
11. Kobayashi, S. Synlett 1994, 689.
12. (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
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15. Purchased from Du Pont.
16. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
17. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
18. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
19. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
20. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
21. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
22. As for metal Nafions, Hg: (a) Olah, G. A. Meidar, D. Synthesis 1978, 671 (b) Saimoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 56, 3078. Si: (c) Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767. Cr, Ce: (d) Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. ibid. 1984, 20, 3317. Al: (e) Waller, F. J. Br. Polym. J. 1984, 76, 239. Ta: (f) Olah, G. A.; Gupta, B.; Farina, M.; Felberg, J. D.; Ip, W. M.; Husain, A.; Karpeles, R.; Lammertsma, K.; Melhotra, A. K.; Trivedi, N. J. J. Am. Chem. Soc. 1985, 107, 7097. See also: (g) Waller, F J. Catal. Rev. Sci. Eng. 1986, 28, 1.
23. 3 and Nafion failed (only 0.1% Sc was included in the polymer (ICP analysis)).
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37. Nafion-Sc (2 g) and Sea Sand (2 g, 15-20 mesh) were combined, and the mixture was packed in a 6 mm glass tube. A carbonyl compound (0.5 mmol) and tetraallyltin (0.5 mmol) were dissolved in acetonitrile (4 mL) and passed through the column using a peristaltic pump (EYELA, MP-3).