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Volumn 44, Issue 49, 2003, Pages 8791-8795

Fluorous reverse-phase silica gel-supported Lewis acids as recyclable catalysts in water

Author keywords

Baeyer Villiger reaction; Diels Alder reaction; Direct esterification; Fluorous; Fluorous reverse phase silica gel; Lewis acid; Recycling; Water

Indexed keywords

ALCOHOL; CARBOXYLIC ACID; LEWIS ACID; LIGAND; SILICA GEL; WATER;

EID: 0242266548     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.183     Document Type: Article
Times cited : (42)

References (32)
  • 2
    • 0032543080 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1174-1196
    • Curran, D.P.1
  • 3
    • 0038372081 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 641-650
    • Horváth, I.T.1
  • 4
    • 0033481596 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 37-41
    • De Wolf, E.1    Van Koten, G.2    Deelman, B.-J.3
  • 5
    • 0347243166 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (1999) J. Fluorine Chem. , vol.94 , pp. 183-193
    • Cavazzini, M.1    Montanari, F.2    Pozzi, G.3    Quici, S.4
  • 6
    • 0003415079 scopus 로고    scopus 로고
    • Fenniri, H., Ed.; Oxford University Press: Oxford; Chapter 11
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (2000) Combinatorial Chemistry , pp. 327-352
    • Curran, D.P.1    Hadida, S.2    Studer, A.3    He, M.4    Kim, S.-Y.5    Luo, Z.6    Larhed, M.7    Hallberg, A.8    Linclau, B.9
  • 7
    • 0036882572 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (2002) J. Fluorine Chem. , vol.118 , pp. 3-17
    • Dobbs, A.P.1    Kimberley, M.R.2
  • 8
    • 0037071139 scopus 로고    scopus 로고
    • Recent reviews: (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196; (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650; (c) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37-41; (d) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183-193; (e) Curran, D. P.; Hadida, S.; Studer, A.; He, M.; Kim, S.-Y.; Luo, Z. ; Larhed, M.; Hallberg, A.; Linclau, B. In Combinatorial Chemistry; Fenniri, H., Ed.; Oxford University Press: Oxford, 2000; Chapter 11, pp. 327-352; (f) Dobbs, A. P.; Kimberley, M. R. J. Fluorine Chem. 2002, 118, 3-17; (g) Tetrahedron Symposium-in-Print No. 91: Fluorous chemistry; Gladysz, J. A.; Curran, D. P., Eds.; 2002; Vol. 58, pp. 3823-4132.
    • (2002) Tetrahedron Symposium-in-Print No. 91: Fluorous Chemistry , vol.58 , pp. 3823-4132
    • Gladysz, J.A.1    Curran, D.P.2
  • 15
    • 0003602022 scopus 로고    scopus 로고
    • John Wiley & SonsNew York
    • Li C.-J., Chan T.-H. Organic Reactions in Aqueous Media. 1997;John Wiley & Sons, New York, Aqueous-Phase Organometallic Catalysis; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998.
    • (1997) Organic Reactions in Aqueous Media
    • Li, C.-J.1    Chan, T.-H.2
  • 23
    • 85030949167 scopus 로고    scopus 로고
    • Into a solution of fluorous Lewis acid (500 mg) in ethanol (20 mL), fluorous reverse-phase silica gel (5 g) was added and the resulting mixture was stirred for 1 h at room temperature. After removal of the solvent under reduced pressure, residual FRPSG-supported Lewis acid was dried under vacuum at 80°C for 6 h
    • Into a solution of fluorous Lewis acid (500 mg) in ethanol (20 mL), fluorous reverse-phase silica gel (5 g) was added and the resulting mixture was stirred for 1 h at room temperature. After removal of the solvent under reduced pressure, residual FRPSG-supported Lewis acid was dried under vacuum at 80°C for 6 h.
  • 24
    • 85030944113 scopus 로고    scopus 로고
    • 2: (a) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433; (b) Corma, A.; Navarro, M. T.; Nemeth, L.; Renz, M. Chem. Commun. 2001, 2190-2191; (c) Murahashi, S.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368; (d) Renz, M.; Blasco, T.; Corma, A.; Fornés, V.; Jansen, R.; Nemeth, L. Chem. Eur. J. 2002, 8, 4708-4717; (e) Berkessel, A.; Andreae, M. R. M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. 2002, 41, 4481-4484; (f) Pillai, U. R.; Sahle-Demessie, E. J. Mol. Cat. A: Chem. 2003, 191, 93-100
    • 2: (a) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433; (b) Corma, A.; Navarro, M. T.; Nemeth, L.; Renz, M. Chem. Commun. 2001, 2190-2191; (c) Murahashi, S.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368; (d) Renz, M.; Blasco, T.; Corma, A.; Fornés, V.; Jansen, R.; Nemeth, L. Chem. Eur. J. 2002, 8, 4708-4717; (e) Berkessel, A.; Andreae, M. R. M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. 2002, 41, 4481-4484; (f) Pillai, U. R.; Sahle-Demessie, E. J. Mol. Cat. A: Chem. 2003, 191, 93-100.
  • 25
    • 85030951648 scopus 로고    scopus 로고
    • 2O (2 mL) and 1,2-dichloroethane (6 mL). Yields of product were determined by GC using n-nonane as an internal standard. FRPSG-supported catalyst was dried under vacuum for reuse in the next cycle. Leaching of Sn(IV) and Hf(IV) in water and 1,2-dichloroethane was analyzed to be less than 5 ppm by ICP-AES
    • 2O (2 mL) and 1,2-dichloroethane (6 mL). Yields of product were determined by GC using n-nonane as an internal standard. FRPSG-supported catalyst was dried under vacuum for reuse in the next cycle. Leaching of Sn(IV) and Hf(IV) in water and 1,2-dichloroethane was analyzed to be less than 5 ppm by ICP-AES.
  • 26
    • 85030935061 scopus 로고    scopus 로고
    • 2NH (4 mol%) was also less active (44% yield, 48% selec.)
    • 2NH (4 mol%) was also less active (44% yield, 48% selec.).
  • 27
    • 85030952286 scopus 로고    scopus 로고
    • 4, the filtrate was a mixture of an aqueous solution, an organic solution, and a suspension containing Sn(IV)
    • 4, the filtrate was a mixture of an aqueous solution, an organic solution, and a suspension containing Sn(IV).
  • 29
    • 0034634399 scopus 로고    scopus 로고
    • Direct esterification catalyzed by Hf(IV) salt: (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140-1142; (b) Ishihara, K.; Nakayama, M.; Ohara, S.; Yamamoto, H. Synlett 2001, 1117-1120; direct esterification by FBC: (c) Xiang, J.; Orita, A.; Otera, J. Angew. Chem., Int. Ed. 2002, 41, 4117-4119.
    • (2000) Science , vol.290 , pp. 1140-1142
    • Ishihara, K.1    Ohara, S.2    Yamamoto, H.3
  • 30
    • 0034930214 scopus 로고    scopus 로고
    • Direct esterification catalyzed by Hf(IV) salt: (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140-1142; (b) Ishihara, K.; Nakayama, M.; Ohara, S.; Yamamoto, H. Synlett 2001, 1117-1120; direct esterification by FBC: (c) Xiang, J.; Orita, A.; Otera, J. Angew. Chem., Int. Ed. 2002, 41, 4117-4119.
    • (2001) Synlett , pp. 1117-1120
    • Ishihara, K.1    Nakayama, M.2    Ohara, S.3    Yamamoto, H.4
  • 31
    • 85047699868 scopus 로고    scopus 로고
    • Direct esterification catalyzed by Hf(IV) salt: (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140-1142; (b) Ishihara, K.; Nakayama, M.; Ohara, S.; Yamamoto, H. Synlett 2001, 1117-1120; direct esterification by FBC: (c) Xiang, J.; Orita, A.; Otera, J. Angew. Chem., Int. Ed. 2002, 41, 4117-4119.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4117-4119
    • Xiang, J.1    Orita, A.2    Otera, J.3
  • 32
    • 85030942421 scopus 로고    scopus 로고
    • 4 (5 mol%) in 1,2-dichloroethane (1.5 mL), methacrylic acid (0.5 mmol) and methanol (3 mmol) was added. Reaction mixture was stirred at 60°C for 16 h. Supported catalyst was recovered by filtration and washed with 1,2-dichloroethane (5 mL). Yields of product were determined by GC using naphthalene as an internal standard
    • 4 (5 mol%) in 1,2-dichloroethane (1.5 mL), methacrylic acid (0.5 mmol) and methanol (3 mmol) was added. Reaction mixture was stirred at 60°C for 16 h. Supported catalyst was recovered by filtration and washed with 1,2-dichloroethane (5 mL). Yields of product were determined by GC using naphthalene as an internal standard.


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