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Volumn 125, Issue 19, 2003, Pages 5861-5872

Fluorous catalysis under homogeneous conditions without fluorous solvents: A "greener" catalyst recycling protocol based upon temperature-dependent solubilities and liquid/solid phase separation

Author keywords

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Indexed keywords

ORGANIC LIQUIDS;

EID: 0037955542     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029241s     Document Type: Article
Times cited : (195)

References (72)
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    • Selected full papers with extensive literature background: (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696. (c) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945. (d) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866. (e) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
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    • 0033620372 scopus 로고    scopus 로고
    • Selected full papers with extensive literature background: (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696. (c) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945. (d) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866. (e) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
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    • Selected full papers with extensive literature background: (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696. (c) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945. (d) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866. (e) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
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    • Selected full papers with extensive literature background: (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696. (c) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945. (d) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866. (e) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
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    • Selected full papers with extensive literature background: (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133. (b) Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696. (c) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945. (d) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866. (e) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
    • (2001) Eur. J. Org. Chem. , pp. 181
    • Colonna, S.1    Gaggero, N.2    Montanari, F.3    Pozzi, G.4    Quici, S.5
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    • For essays on the "ideal recoverable catalyst", see: (a) Gladysz, J. A. Pure Appl. Chem. 2001, 73, 1319. (b) Gladysz, J. A. Chem. Rev. 2002, 102, 3214.
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    • 0035742298 scopus 로고    scopus 로고
    • For essays on the "ideal recoverable catalyst", see: (a) Gladysz, J. A. Pure Appl. Chem. 2001, 73, 1319. (b) Gladysz, J. A. Chem. Rev. 2002, 102, 3214.
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    • U.S. patent 5, 888, 650 (filed June 3, 1996)
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    • Dissertation
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    • note
    • 13 would have been another obvious choice, but an efficient fluorous catalyst has not yet been developed.
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    • note
    • The solubility data are not corrected for any change in solvent volume with temperature.
  • 50
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    • note
    • Under the conditions of this experiment (which has no n-octane extraction), Figure 2 predicts (for phase separation at -20 °C) ca. 0.17% leaching of 1a per cycle.
  • 51
    • 0038162550 scopus 로고    scopus 로고
    • note
    • All recycling experiments employ a 2.0:1.0 2/3 mol ratio. Under these conditions, I should be a less long-lived state.
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    • (a) Tzschucke, C. C.; Markert, C.; Glatz, H.; Bannworth, W. Angew. Chem. Int. Ed. 2002, 41, 4500; Angew. Chem. 2002, 114, 4678.
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    • note
    • Because the homogeneous catalysis literature is so vast, and electronic search methods are not capable of systematically retrieving such data, there are likely precedents that have escaped our attention. For example, considering the numerous amine-catalyzed reactions, many of which are conducted at elevated temperature, it would not be surprising to find scattered examples. However, we are confident that for whatever cases that might exist, there would be little chance of developing a general family of catalysts encompassing the breadth of molecules represented by 1a,b and Figure 7.
  • 72
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    • note
    • 3/1a response factor of 0.999.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.