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Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis
Abstract
Recovery and purification difficulties can limit the yield and utility of otherwise successful organic synthesis strategies. A “fluorous synthesis” approach is outlined in which organic molecules are rendered soluble in fluorocarbon solvents by attachment of a suitable fluorocarbon group. Fluorocarbon solvents are usually immiscible in organic solutions, and fluorous molecules partition out of an organic phase and into a fluorous phase in a standard liquid-liquid extraction. Simple yet substantive separations of organic reaction mixtures are achieved without resorting to chromatography. Because fluorous synthesis combines in many respects the favorable purification features of solid-phase synthesis with the favorable reaction, identification, and analysis features of traditional organic synthesis, it should prove valuable in the automated synthesis of libraries of individual pure organic compounds.
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“In fact, perfluorocarbons are poorly soluble in organic solvents and thus can form a third ‘fluorous phase’ when added to a two‐phase water/organic solvent mixture (Studer et al., 1997; Dobbs and Kimberley, 2002).”
From Nothing lasts forever: understanding microbial biodegradation of polyfluorinated compounds and perfluorinated alkyl substances (2022) · cites this paper as Studer et al., 1997
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Cites
Protective Groups in Organic Synthesis
Greene, T. W., & Wuts, P. G. M. (1999) · Wiley eBooks · doi:10.1002/0471220574 · Cited by 5,677
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Padwa, A. (1984) · Medical Entomology and Zoology · Cited by 3,241
Protective groups in organic synthesis
Hodge, P. (1992) · Polymer · doi:10.1016/0032-3861(92)91123-j · Cited by 2,216
Synthesis and Applications of Small Molecule Libraries
Thompson, L. A., & Ellman, J. A. (1996) · Chemical Reviews · doi:10.1021/cr9402081 · Cited by 1,452
Facile Catalyst Separation Without Water: Fluorous Biphase Hydroformylation of Olefins
Horváth, I. T., & Rábai, J. (1994) · Science · doi:10.1126/science.266.5182.72 · Cited by 1,416
100 years of the biginelli dihydropyrimidine synthesis
Oliver Kappe, C. (1993) · Tetrahedron · doi:10.1016/s0040-4020(01)87971-0 · Cited by 1,228
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Multiple-Component Condensation Strategies for Combinatorial Library Synthesis
Armstrong, R. W., Combs, A. P., Tempest, P. A., Brown, S. D., & Keating, T. A. (1996) · Accounts of Chemical Research · doi:10.1021/ar9502083 · Cited by 1,111
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Cited by
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165
Metadata
- Authors
- Studer, A., Hadida, S., Ferritto, R., Kim, S.-Y., Jeger, P., Wipf, P., & Curran, D. P.
- Affiliations
- Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
- Venue
- Science
- Published
- 1997-02-07
- Volume
- 275
- Issue
- 5301
- Pages
- 823-826
- ISSN
- 0036-8075
- 1095-9203
- Cited by
- 470
- References
- 29
- Language
- en
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