메뉴 건너뛰기




Volumn 122, Issue 30, 2000, Pages 7202-7207

Organic synthesis inside particles in water: Lewis acid - surfactant-combined catalysts for organic reactions in water using colloidal dispersions as reaction media

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ANIONIC SURFACTANT; DODECANE; DODECYL SULFATE; SURFACTANT; WATER;

EID: 0034596298     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001420r     Document Type: Article
Times cited : (312)

References (60)
  • 1
    • 0004252595 scopus 로고    scopus 로고
    • Blacky Academic and Professional: London
    • Reviews for organic synthesis in water: (a) Organic Synthesis in Water, Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, John Wiley & Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous- Phase Organometallic Chemistry: Concepts and Applications; Wiley- VCH: Weinheim, 1998.
    • (1998) Organic Synthesis in Water
    • Grieco, P.A.1
  • 2
    • 0003602022 scopus 로고    scopus 로고
    • John Wiley & Sons: New York
    • Reviews for organic synthesis in water: (a) Organic Synthesis in Water, Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, John Wiley & Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous- Phase Organometallic Chemistry: Concepts and Applications; Wiley- VCH: Weinheim, 1998.
    • (1997) Organic Reactions in Aqueous Media
    • Li, C.-J.1    Chan, T.-H.2
  • 3
    • 0003476436 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim
    • Reviews for organic synthesis in water: (a) Organic Synthesis in Water, Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, John Wiley & Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998.
    • (1998) Aqueous-Phase Organometallic Chemistry: Concepts and Applications
    • Cornils, B.1    Herrmann, W.A.2
  • 20
    • 0002384652 scopus 로고    scopus 로고
    • Grieco, P. A., Ed.; Blacky Academic and Professional: London
    • (c) Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998; p 262.
    • (1998) Organic Synthesis in Water , pp. 262
    • Kobayashi, S.1
  • 32
    • 0342735575 scopus 로고    scopus 로고
    • note
    • Although we also attempted to determine second-order rate constants, their determination was not successful probably due to complicated kinetic behavior caused by hydrolysis of the silyl enol ether and effects of the product on the catalytic efficiency in this colloidal system.
  • 33
    • 0032546286 scopus 로고    scopus 로고
    • In addition, it was revealed that reactions under neat conditions had substrate limitation and sometimes lacked reproducibility of experiments. Kobayashi, S.; Busujima, T.; Nagayama, S. Tetrahedron Lett. 1998, 39, 1579.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1579
    • Kobayashi, S.1    Busujima, T.2    Nagayama, S.3
  • 35
    • 0017398566 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.-I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1977) Tetrahedron Lett. , pp. 3643
    • Ojima, I.1    Inaba, S.-I.2    Yoshida, K.3
  • 36
    • 0005570729 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3643
    • Dubois, J.-E.1    Axiotis, G.2
  • 37
    • 0009244352 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 539
    • Colvin, E.W.1    McGarry, D.G.2
  • 38
    • 0002265572 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1992) Chem. Lett. , pp. 1445
    • Shimada, S.1    Saigo, K.2    Abe, M.3    Sudo, A.4    Hasegawa, M.5
  • 39
    • 0020507552 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4707
    • Ikeda, K.1    Achiwa, K.2    Sekiya, M.3
  • 40
    • 0002573478 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1989) Chem. Lett. , pp. 1397
    • Mukaiyama, T.1    Kashiwagi, K.2    Matsui, S.3
  • 41
    • 0000648419 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1990) Chem. Lett. , pp. 889
    • Mukaiyama, T.1    Akamatsu, H.2    Han, J.S.3
  • 42
    • 84899537455 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1993) Synlett , pp. 141
    • Onaka, M.1    Ohno, R.2    Yanagiya, N.3    Izumi, Y.4
  • 43
    • 0343821220 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1994) Synlett , pp. 963
    • Ishihara, K.1    Funahashi, M.2    Hanaki, N.3    Miyata, M.4    Yamamoto, H.5
  • 44
    • 0001284906 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 1721
    • Ishihara, K.1    Hanaki, N.2    Funahashi, M.3    Miyata, M.4    Yamamoto, H.5
  • 45
    • 0041753278 scopus 로고
    • For a stoichiometric use of a Lewis acid: (a) Ojima, I.; Inaba, S.- I.; Yoshida, K. Tetrahedron Lett. 1977, 3643. (b) Dubois, J.-E.; Axiotis, G. Tetrahedron Lett. 1983, 24, 3643. (C) Colvin, E. W.; McGarry, D. G. J. Chem. Soc., Chem. Commun. 1985, 539. (d) Shimada, S.; Saigo, K.; Abe, M.; Sudo, A.; Hasegawa, M. Chem. Lett. 1992, 1445. For a catalytic use of a Lewis acid: (e) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707. (f) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (g) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (i) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963. (j) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721. (k) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
    • (1995) Synlett , pp. 233
    • Kobayashi, S.1    Araki, M.2    Ishitani, H.3    Nagayama, S.4    Hachiya, I.5
  • 47
    • 0032799972 scopus 로고    scopus 로고
    • Brønsted acid-catalyzed three-component Mannich-type reactions in aqueous media have also been reported: (b) Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1045.
    • (1999) Synlett , pp. 1045
    • Akiyama, T.1    Takaya, J.2    Kagoshima, H.3
  • 51
    • 0342300501 scopus 로고    scopus 로고
    • note
    • When no LASC was used, the reaction of benzaldehyde, o-anisidine, and 1-phenyl-1-trimethylsilylethene in water proceeded sluggishly.
  • 54
  • 56
    • 0002950518 scopus 로고
    • Coordination Chemistry
    • American Chemical Society: Washington, DC
    • (a) Martell, A. E., Ed.; Coordination Chemistry; ACS Monograph 168; American Chemical Society: Washington, DC, 1978; Vol. 2.
    • (1978) ACS Monograph 168 , vol.2
    • Martell, A.E.1
  • 58
    • 0001069588 scopus 로고
    • Effects of water on organic reactions have been discussed. For example: (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159. (b) Otto, S.; Bertoncin, F.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1996, 118, 7702.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 159
    • Breslow, R.1
  • 59
    • 0029813957 scopus 로고    scopus 로고
    • Effects of water on organic reactions have been discussed. For example: (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159. (b) Otto, S.; Bertoncin, F.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1996, 118, 7702.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7702
    • Otto, S.1    Bertoncin, F.2    Engberts, J.B.F.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.