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Technical References

Publications & patents from FTI scientists and our Colleagues


Links to the pdf-version of papers are provided for convenience where available. Users must have Acrobat Reader (Download the free Acrobat Reader) as well as access to the journal sites.


 

Table of Contents

 

General Reviews

  1. Curran, D. P. “Organic Synthesis with Light-Fluorous Reagents, Reactants, Catalysts, and Scavengers” Aldrichmica Acta 2006, 39, 3-9.
  2. Chen, C. H.-T.; Zhang, W. “Fluorous Reagents and Scavengers versus Solid-Supported Reagents and Scavengers, A Reaction Rate and Kinetic Comparison” Mol. Diversity 2005 9, 353-359.
  3. Zhang, W. “Fluorous Tagging Strategy for Solution-Phase Synthesis of Small Molecules, Peptides and Oligosaccharides” Curr. Opin. Drug Disc. Dev. 2004, 7, 784-797.
  4. Hawes, P. A. "Hit the fluor " Modern Drug Discovery, Dec. 2004, 51-53
  5. Zhang, W. "Fluorous Synthesis of Heterocyclic Systems" Chem. Rev, 2004, 104 , 2531-2556.
  6. W. Zhang, "Fluorous Technologies for Solution-Phase High-Throughput Organic Synthesis" Tetrahedron Report Tetrahedron 2003, 59, 4475-4489.
  7. D. P. Curran, "Fluorous methods for parallel and combinatorial synthesis" Pharmaceutical News, in press.
  8. J. A. Gladysz, D. P. Curran, "Fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond" Tetrahedron 2002, 58, 3823-3825. [Full Article - PDF]
  9. Curran, D. P.; Luo, Z. "Fluorous Techniques for the Synthesis and Separation of Organic Molecules" Green Chem. 2001 , 3 , G3.
  10. D. P. Curran, S. Hadida, A. Studer, M. He, S.-Y. Kim, Z. Luo, M. Larhed, M. Hallberg, B. Linclau, "Fluorous Synthesis: A User's Guide", In Combinatorial Chemistry: A Practical Approach; H. Fenniri, Ed.; Oxford Univ Press: Oxford, 2000; Vol. 2; pp 327-352
  11. D. P. Curran, "Fluorous Techniques for the Synthesis of Organic Molecules: A Unified Strategy for Reaction and Separation", in Stimulating Concepts in Chemistry", Wiley-VCH 2000, 25-37.
  12. J. J. Maul, P. J. Ostrowski, G. A. Ublacker, B. Linclau, D. P. Curran "Benzotrifluoride and related solvents in organic synthesis", In Topics in Current Chemistry, Modern Solvents in Organic Synthesis"; P. Knochel, Ed.; Springer-Verlag: Berlin, 1999; Vol. 206; pp 80-104.
  13. D. P. Curran, "Strategy-level separations in organic synthesis: From planning to practice", Angew. Chem. Int. Ed. Engl. 1998, 37, 1175-1196. [Full Article - PDF]
  14. D. P. Curran, "Combinatorial Organic Synthesis and Phase Separation: Back to the Future", Chemtracts - Org. Chem. 1996, 9, 75-87.

Microwave-Assisted Fluorous Synthesis

  1. Zhang, W. “Microwave-Enhanced High-Speed Fluorous Synthesis” in Microwave Methods in Organic Synthesis; Topics Curr. Chem. Vol. 266, Larhed, M.; Olofsson, K. Eds.; Springer, 2006, pp145-166.
  2. Zhang, W. “Microwave-Enhanced Fluorous Synthesis” Chimica Oggi (Chemistry Today), 2005, 23 (3): XI-XIII.
  3. Lu, Y.; Zhang, W. “Microwave-Assisted Synthesis of a 3-Aminoimidazo[1,2-a]-pyridine/pyrazine Library by Fluorous Multicomponent Reactions and Subsequent Cross-Coupling Reactions” QSAR Comb. Sci. 2004, 23, 827-835.
  4. Zhang, W. Tempest, P. "Highly efficient microwave-assisted fluorous Ugi and post-condensation reactions for benzimidazoles and quinoxalinones" Tetrahedron Lett. 2004, 45, 45, 6757-6760.

  5. Zhang, W.; Nagashima, T.; Lu, Y.; Chen, C. H.-T. "A traceless perfluorooctylsulfonyl tag for deoxygenation of phenols under microwave irradiation" Tetrahedron Lett. 2004, 45, 4611-4613.

  6. Zhang, W.; Chen, C. H.-T.; Luo, Y.; Nagashima T. "A Highly Efficient Microwave-Assisted Fluorous Suzuki Coupling Reaction" Org. Lett . 2004, 6, 1473-1476.
  7. Zhang, W.; Lu, Y.; Chen, C. H-T "Combination of Microwave Reactions with Fluorous Separations in the Palladium-Catalyzed Synthesis of Aryl Sulfides" Molecular Diversity, 2003, 7, 199-202.

 

Fluorous Separations

  1. Zhang, W.; Curran, D. P. “Synthetic applications of fluorous solid-phase extraction (F-SPE)” Tetrahedron 2006, 62, 11837–11865
  2. Zhang, W.; Lu, Y.; Chen, C. H.-T. Zeng, L.; Kassel, D. B. “Fluorous Mixture Synthesis of Two Libraries with Hydantoin- and Benzodiazepinedione-Fused Heterocyclic Scaffolds” J. Comb. Chem. 2006, 8, 687-695.
  3.  Zhang, W.; Lu, Y. “Automation of Fluorous Solid-Phase Extraction for Parallel Synthesis” J. Comb. Chem 2006, 8, 890-896.
  4. Curran, D. P.; Bajpai, R.; Sanger, E. “Purification of fluorous Mitsunobu reactions by liquid-liquid extraction” Adv. Synth. Catal. 2006, 348, 1621 – 1624.
  5. Zhang, W.; Curran, D. P. “Synthetic applications of fluorous solid-phase extraction (F-SPE)” Tetrahedron 2006, 62, 11837–11865
  6. Zhang, W.; Lu, Y.; Chen, C. H.-T. Zeng, L.; Kassel, D. B. “Fluorous Mixture Synthesis of Two Libraries with Hydantoin- and Benzodiazepinedione-Fused Heterocyclic Scaffolds” J. Comb. Chem. 2006, 8, 687-695.
  7.  Zhang, W.; Lu, Y. “Automation of Fluorous Solid-Phase Extraction for Parallel Synthesis” J. Comb. Chem 2006, 8, 890-896.
  8. Curran, D. P.; Bajpai, R.; Sanger, E. “Purification of fluorous Mitsunobu reactions by liquid-liquid extraction” Adv. Synth. Catal. 2006, 348, 1621 – 1624.
  9. Koichi Mikami, Hiroshi Matsuzawa, Seiji Tekeuchi, Yutaka Nakamura, Dennis P. Curran “Beta-Cyclodextrin Columns for Separation of Fluorous and Non-Fluorous Compounds: How To Use b-Cyclodextrin Columns in Fluorous Mixture Synthesis and Racemic Synthesis”Synlett 2004, 2713–2716.2004.
  10. Curran DP, Dandapani S, Werner S, Matsugi, M. “Fluorous columns are superior to cyclodextrin columns for demixing in fluorous mixture synthesis: When and why to use fluorous silica gel” Synlett 2004, 1545-1548.
  11. Yu, M. S.; Curran, D. P.; Nagashima, T. “Increasing Fluorous Partition Coefficients by Solvent Tuning” Org. Lett. 2005, 7, 3677-3680.
  12. Zhang, W.; Lu, Y.; Nagashima, T. “Plate-to-Plate Fluorous Solid-Phase Extraction for Solution-Phase Parallel Synthesis” J. Comb. Chem. 2005, 7, 893–897.
  13. D. P. Curran, "Fluorous reverse phase silica gel. A new tool for preparative separations in synthetic organic and organofluorine chemistry" Synlett 2001, 1488-1496.
  14. D. P. Curran; Y. Oderaotoshi, "Thiol additions to acrylates by fluorous mixture synthesis: Relative control of elution order in demixing by the fluorous tag and the thiol substituent", Tetrahedron, 2001, 47, 5243. [Full Article - PDF]
  15. N. Spetseris, S. Hadida, D. P. Curran, T. Y. Meyer "Organic/fluorous phase extraction: A new tool for the isolation of organometallic complexes" Organometallics 1998, 17, 1458-1459.
  16. S. Kainz, Z. Y. Luo, D. P. Curran, W. Leitner "Synthesis of perfluoroalkyl-substituted aryl bromides and their purification over fluorous reverse phase silica" Synthesis 1998, 1425-1437.
  17. S. Hadida, M. S. Super, E. J. Beckman, D. P. Curran, "Radical reactions with alkyl and fluoroalkyl (fluorous) tin hydride reagents in supercritical CO2", J. Am. Chem. Soc. 1997, 119, 7406-7407. [Full Article - PDF]
  18. D. P. Curran, S. Hadida, M. He, "Thermal allylations of aldehydes with a fluorous allylstannane. Separation of organic and fluorous products by solid phase extraction with fluorous reverse phase silica gel", J. Org. Chem. 1997, 62, 6714-6715. [Full Article - PDF]

Fluorous Mixture Syntheses of Natural Product and Drug-like Molecules

  1. Zhang, W.; Lu, Y.; Chen, C. H.-T. Zeng, L.; Kassel, D. B. “Fluorous Mixture Synthesis of Two Libraries with Hydantoin- and Benzodiazepinedione-Fused Heterocyclic Scaffolds” J. Comb. Chem. 2006, 8, 687-695.
  2. Yoshikazu Fukui, Arndt M. Brückner, Youseung Shin, Raghavan Balachandran, Billy W. Day, and Dennis P. Curran “Fluorous Mixture Synthesis of (-)-Dictyostatin and Three Stereoisomers” Org. Lett. 2006, 8, 301-304.
  3. Venugopal Gudipati, Dennis P. Curran, and Craig S. Wilcox “Solution-Phase Parallel Synthesis with Oligoethylene Glycol Sorting Tags. Preparation of All Four Stereoisomers of the Hydroxybutenolide Fragment of Murisolin and Related Acetogenins” J. Org. Chem. 2006, 71, 3599-3607.
  4. Dennis P. Curran, Gustavo Moura-Letts, Matthias Pohlman “Solution-Phase Mixture Synthesis with FluorousTagging En Route: Total Synthesis of an Eight-Member Stereoisomer Library of Passifloricins” Angew. Chem. Int. Ed. 2006, 45, 2423 –2426.
  5. Curran, D. P.; Zhang, Q. S.; Richard, C.; Lu, H. J.; Gudipati, V.; Wilcox, C. S. “Total synthesis of a 28-member stereoisomer library of murisolins” J. Am. Chem. Soc. 2006, 128, 9561-9573.
  6. Fanglong Yang and Dennis P. Curran “Structure Assignment of Lagunapyrone B by Fluorous Mixture Synthesis of Four Candidate Stereoisomers” J. Am. Chem. Soc. 2006, 128, 14200-14205
  7. Qisheng Zhang, Dennis P. Curran “Quasienantiomers and Quasiracemates: New Tools for Identification, Analysis, Separation,and Synthesis of Enantiomers’ Chem. Eur. J. 2005, 11, 4866 – 4880.
  8. Craig S. Wilcox, Venugopal Gudipati, Hejun Lu, Serhan Turkyilmaz, and Dennis P. Curran “Solution-Phase Mixture Synthesis with Double-Separation Tagging: Double Demixing of a Single Mixture Provides a Stereoisomer Library of 16 Individual Murisolins” Angew. Chem. Int. Ed. 2005, 44, 6938 –6940.
  9. Sivaraman Dandapani, Mario Jeske, and Dennis P. Curran “Synthesis of All 16 Stereoisomers of Pinesaw Fly Sex Pheromones Tools and Tactics for Solving Problems in Fluorous Mixture Synthesis” J. Org. Chem. 2005, 70, 9447-9462.
  10. Huahua Jian and James M. Tour “Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s” J. Org. Chem. 2005, 70, 3396-3424.
  11. Manku S, Curran DP “Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates” J. Org. Chem. 2005, 70, 4470-4473.
  12. Manku S, Curran DP “Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes” J. Comb. Chem. 2005, 7, 63-68.
  13. T. Nagashima, W. Zhang. "Solution-Phase Parallel Synthesis of an N-Alkylated Dihydropteridinone Library from Fluorous Amino Acids " J. Comb. Chem. 2004 , 6, 942-949
  14. Zhang, W. "Fluorous Mixture Synthesis (FMS) of Enantiomers, Diastereomers, and Compound Libraries", account article for Arkivoc 2004 (i), 101-109.
  15. Zhang, W. "Fluorous Mixture Syntheses (FMS)" Chimica Oggi (Chemistry Today) 2003.
  16. Q. Zhang, A. Rivkin, A., D. P. Curran "Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappacine" J. Am. Chem. Soc. 2002, 124, 5774. [Full Article - PDF]
  17. D. P. Curran, T. Furukawa "Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixtures synthesis" Org. Lett. 2002, 4, 2233. [Full Article - PDF]
  18. Z. Luo, Q. Zhang, Y. Oderaotoshi and D. P. Curran, "Fluorous Mixture Synthesis: A Fluorous-Tagging Strategy for the Synthesis and Separation of Mixtures of Organic Compounds" Science 2001, 291, 1766-1769. [Full Article - PDF]
  19. D. P. Curran; Y. Oderaotoshi, "Thiol additions to acrylates by fluorous mixture synthesis: Relative control of elution order in demixing by the fluorous tag and the thiol substituent", Tetrahedron, 2001, 47, 5243. [Full Article - PDF]
  20. Y. Shin, N. Choy, R. Balachandran, C. Madiraju, B. W. Day, D. P. Curran, P. Curran, "Discodermolide/dictyostatin hybrids: Synthesis and biological evaluation" Org. Lett., 2002, 4, 4443.
  21. W. Zhang, Z. Luo, C. H. T. Chen, D. P. Curran, "Solution-Phase Preparation of a 560-Compound Library of Individual Pure Mappicine Analogues by Fluorous Mixture Synthesis" J. Am. Chem. Soc., 2002, 124, 10443.
  22. W. Zhang, Z. Luo, C. H.-T. Chen, D. P. Curran "Solution-phase preparation of a 560-compound library of individually pure mappicine analogs by fluorous mixture synthesis" J. Am. Chem. Soc., 2002, 124, 10443. [Full Article - PDF]

Fluorous Reagents

  1. Zhang, W.; Lu, Y. “Fluorous 2,4-Dichloro-1,3,5-triazine (F-DCT) as an Amide Coupling Agent” QSAR Comb. Sci. 2006, 25, 724-727.
  2. Chen, C. H.-T.; Zhang, W. “Fluorous Reagents and Scavengers versus Solid-Supported Reagents and Scavengers, A Reaction Rate and Kinetic Comparison” Mol. Diversity 2005, 9, 353-359.
  3. Curran DP, Wang XA, Zhang QS “Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines” J. Org. Chem. 2005, 70, 3716-3719.
  4. Dandapani, S.; Curran, D.P.; “Separation-Friendly Mitsunobu Reactions: A Microcosm of Recent Developments in Separation Strategies” Chem. Eur. J. 2004, 3130-3138.
  5. Dandapani, S.; Curran, D.P.; “Second Generation Fluorous DEAD Reagents Have Expanded Scope in the Mitsunobu Reaction and Retain Convenient Separation Features” J. Org. Chem. 2004, 69, 8751-8757.
  6. Nagashima, T.; Petro, M. J.; Zhang, W. “Fluorous 2-Chloropyridinium Salt (Mukaiyama Condensation Reagent) for Amide Formation Reaction” Tetrahedron Lett. 2005, 6, 6585-6589.
  7. Zhang, W. “Fluorous Tagging Strategy for Solution-Phase Synthesis of Small Molecules, Peptides and Oligosaccharides” Curr. Opin. Drug Disc. Dev. 2004, 7, 784-797.
  8. Chen, C. H.-T.; Zhang, W. "FluoMar, a Fluorous Version of the Marshall Resin for Solution-Phase Library Synthesis" Org. Lett. 2003, 5, 1015.
  9. Lu, Y.; Zhang, W. "Fluorous TIPS Triflate" Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS), article RN00424, Wipf, P. Ed., Wiley, 2004.
  10. S. Dandapani, D. P. Curran "Fluorous Mitsunobu reagents and reactions" Tetrahedron 2002, 58, 3855-64. [Full Article - PDF]
  11. Q. S. Zhang, Z. Y. Luo, D. P. Curran "Separation of "light fluorous" reagents and catalysts by fluorous solid-phase extraction: Synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags" J. Org. Chem. 2000, 65, 8866-8873. [Full Article - PDF]
  12. B. Bucher, D. P. Curran "Selective sulfonylation of 1,2-diols and derivatives catalyzed by a recoverable fluorous tin oxide" Tetrahedron Lett. 2000, 41, 9617-9621. [Full Article - PDF]
  13. I. Ryu, T. Niguma, S. Minakata, M. Komatsyu, Z. Y. Luo, D. P. Curran "Radical carbonylations with fluorous allyltin reagents" Tetrahedron Lett. 1999, 40, 2367-2370. [Full Article - PDF]
  14. K. Olofsson, S. Y. Kim, M. Larhed, D. P. Curran, A. Hallberg "High-speed, highly fluorous organic reactions" J. Org. Chem. 1999, 65, 4539-4541. [Full Article - PDF]
  15. D. P. Curran, S. Hadida, S. Y. Kim, "Tris(2-perfluorohexylethyl) tin azide: A new agent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous organic liquid-liquid extraction" Tetrahedron 1999, 55, 8997-9006. [Full Article - PDF]
  16. D. P. Curran, S. Hadida, S. Y. Kim, Z. Y. Luo "Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions" J. Am. Chem. Soc. 1999, 6607-6615. [Full Article - PDF]
  17. D. P. Curran "Fluorous methods for synthesis and separation of organic molecules" Pure Appl. Chem. 2000, 72, 1649-1653.
  18. D. P. Curran, "Parallel synthesis with fluorous reagents and reactants", Med. Res. Rev. 1999, 19, 432-438.

Fluorous Scavengers

  1. Lu, Y.; Zhang, W. “Fluorous 2,4-Dichloro-1,3,5-triazine (F-DCT) as Nucleophile Scavengers” QSAR Comb. Sci. 2006, 25, 728-731.
  2. Zhang, W.   “Fluorous Scavenging” in Hand Book of Fluorous Chemistry, Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp473-474. T. Eds. Wiley-VCH, 2004, pp473-474.
  3. Chen, C. H-T.; Zhang, W. "Fluorous Thiol" Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS), article RN00425, P. Wipf, Ed. Wiley, 2004.
  4. Zhang, W. "Fluorous Scavengers for Solution-Phase Synthesis" PharmaChem Directory, 2003, pp18-20.
  5. W. Zhang, C. H.-T. Chen, T. Nagashima, "Fluorous Electrophilic Scavengers for Solution-Phase Parallel Synthesis", Tetrahedron Lett. 2003, 44, 2065-68.
  6. W. Zhang, D. P. Curran, C. H.-T. Chen "Use of fluorous silica gel to separate fluorous thiol quenching derivatives in solution-phase parallel synthesis" Tetrahedron 2002, 58, 3871-75. [Full Article - PDF]
  7. B. Linclau, A. K. Singh, D. P. Curran, "Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis", J. Org. Chem. 1999, 64, 2835-2842. [Full Article - PDF]

Fluorous Protecting Groups

  1. Zhang, W.; Williams, J. A.; Lu, Y.; Nagashima, T.; Chu, Q.  “Fluorous Synthesis of Sclerotigenin-Type Benzodiazepine-Quinazolinones” Tetrahedron Lett. 2007, 48, 563-565.
  2. Zhang,W.; Nagashima, T. “Palladium-Catalyzed Buchwald–Hartwig Type Amination of Fluorous Arylsulfonates” J. Fluorine Chem. 2006, 127, 588-591.
  3. Zhang, W.; Lu, Y.; Geib, S.  “Synthesis of Fluorous and Non-Fluorous Polycyclic Systems by One-Pot, Double Intramolecular 1,3-Dipolar Cycloaddition of Azomethine Ylides” Org. Lett. 2005, 7, 2269-2272.
  4. Zhang, W.; Chen, C. H.-T. “Fluorous Synthesis of Biaryl-Substituted Proline Analogs by 1,3-Dipolar Cycloaddition and Suzuki Coupling Reactions” Tetrahedron Lett. 2005, 46, 1807-1810.
  5. Lu, Y.; Zhang, W. “Fluorous Parallel Synthesis of a Hydantoin/Thiohydantoin Library” Mol. Diversity 2005, 9, 91-98.
  6. Nagashima, T.; Zhang W. “Fluorous Parallel Synthesis of an N-Alkylated Dihydropteridinone Library” J. Comb. Chem. 2004, 6, 942-949.
  7. Zhang, W.   “Fluorous Protecting Groups and Tags ” in Hand Book of Fluorous Chemistry, Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp222-236.
  8. Lu, Y.; Zhang, W. "Fluorous Parallel Synthesis of a Hydantoin/Thiohydantoin Library" Molecular Diversity , 2004, in press.
  9. Zhang, W. "Fluorous Protecting Groups and Tags for Solution-Phase Synthesis" Speciality Chemistry Magazine, 2004, 25 (5) , 30-32 .
  10. Zhang, W.; Lu, Y. "Fluorous Synthesis of Hydantoins and Thiohydantoins" Org. Lett . 2003 , 5, 2555.
  11. Curran, D. P.; Amatore, M.; Campbell, M.; Go, E.; Guthrie, D.; Luo, Z. "Synthesis and Reactions of Fluorous Carbobenzyloxy (FCbz) Derivatives of Alpha-amino Acids"   J. Org. Chem. 2003, 68, 4643. 
  12. Chen, C. H-T.; Zhang, W. "Fluorous Thiol" Electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS), article RN00425, P. Wipf, Ed. Wiley, 2004.
  13. Luo, Z.; Williams, J.; Read, R.; Curran, D. P. “Fluorous Boc (FBoc) Carbamates: New Amine Protecting Groups for Use in Fluorous Synthesis” J. Org. Chem. 2001 , 66 , 4261.  
  14. Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z., "Synthesis and Reactions of Fluorous Carbobenzyloxy (fCbz) Derivatives of a-Amino Acids", Journal of Organic Chemistry 2003, 68, 4643-4647 [Full Article-PDF]
  15. C. H.-T. Chen, W. Zhang, "FluoMar, a Fluorous Version of the Marshall Resin for Solution-Phase Library Synthesis", Org. Lett. 2003, 5, 1015-17.
  16. W. Zhang, "Fluorous synthesis of Disubstituted Pyrimidines", Org. Lett. 2003, 5, 1011-13.
  17. D. P. Curran, Z. Y. Luo, "Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse phase silica gel", J. Am. Chem. Soc. 1999, 121, 9069-9072. [Full Article - PDF]
  18. Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D. P. "Fluorous Boc ((F)Boc) carbamates: New amine protecting groups for use in fluorous synthesis" J. Org. Chem. 2001, 66, 4261-4266. [Full Article - PDF]

Fluorous Catalytic Reactions

  1. Gustavo Moura-Letts and Dennis P. Curran “Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene-Diene Cross Metathesis” Org. Lett. 2007, 9, 5 – 8.
  2. Chu, Q.; Zhang, W.; Curran, D. P. “A Recyclable Fluorous Organocatalyst for Diels-Alder Reactions” Tetrahedron Lett. 2006, 47, 9287-9290.
  3. Matsugi M, Curran DP “Synthesis, reaction, and recycle of light fluorous Grubbs-Hoveyda catalysts for alkene metathesis” J. Org. Chem. 2005, 70, 1636-1642.
  4. Curran DP, Fischer K, Moura-Letts G “A soluble fluorous palladium complex that promotes Heck reactions and can be recovered and reused” Synlett 2004, 1379-1382.
  5. Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, "Recyclable fluorous chiral ligands and catalysts: asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by fluorous BINol-Ti complexes", Tetrahedron 2002, 58, 3963-3969. [Full Article - PDF]
  6. Y. Nakamura, S. Takeuchi, Y. Ohgo, D. P. Curran, "Preparation of a fluorous chiral BINol derivative and application to an asymmetric protonation reaction", Tetrahedron 2000, 56, 351-356. [Full Article - PDF]
  7. Y. Nakamura, S. Takeuchi, Y. Ohgo, D. P. Curran, "Asymmetric alkylation of aromatic aldehydes with diethylzinc catalyzed by a fluorous BINol-Ti complex in an organic and fluorous biphase system", Tetrahedron Lett. 2000, 41, 57-60. [Full Article - PDF]
  8. I. Ryu, T. Niguma, S. Minakata, M. Komatsu, S. Hadida, D. P. Curran, "Hydroxymethylation of organic halides. Evaluation of a catalytic system involving a fluorous tin hydride reagent for radical carbonylation", Tetrahedron Lett. 1997, 38, 7883-7886. [Full Article - PDF]

Fluorous Synthesis and Purification of Peptides and Oligos

  1. Zhang, W. "Fluorous Tagging Strategy for solution-phase synthesis of small molecules, peptides, and oligosaccharides" Current Opinion in Drug Discovery and Development 2004 7(6):784-797
  2. Zhang, W. “Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides” In ACS Symposium Series: Current Fluoroorganic Chemistry. New Synthetic Directions, Technologies, Materials and Biological Applications; Soloshonok, V. A.; Mikami, K. Yamazaki, T.; Welch, J. T., and Honek, J Eds. Oxford University Press, 2006, pp207-220.

Fluorous Multi-Component Reactions

  1. Zhang, W. “Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds” Comb. Chem. High Throughput Screening 2007, 10. 219-229.
  2. Zhang, W.; Lu, Y.; Geib, S.  “Synthesis of Fluorous and Non-Fluorous Polycyclic Systems by One-Pot, Double Intramolecular 1,3-Dipolar Cycloaddition of Azomethine Ylides” Org. Lett. 2005, 7, 2269-2272.
  3. Zhang, W.; Chen, C. H.-T. “Fluorous Synthesis of Biaryl-Substituted Proline Analogs by 1,3-Dipolar Cycloaddition and Suzuki Coupling Reactions” Tetrahedron Lett. 2005, 46, 1807-1810.
  4. Lu, Y.; Zhang, W. “Microwave-Assisted Synthesis of a 3-Aminoimidazo[1,2-a]-pyridine/pyrazine Library by Fluorous Multicomponent Reactions and Subsequent Cross-Coupling Reactions” QSAR Comb. Sci. 2004, 23, 827-835.
  5. Zhang, W. Tempest, P. “Highly Efficient Microwave-Assisted Fluorous Ugi and Post-Condensation Reactions for Benzimidazoles and Quinoxalinones” Tetrahedron Lett. 2004, 45, 6757-6760.

Fluorous Diversity-Oriented Synthesis

  1. Zhang, W.; Lu, Y.; Chen, C. H.-T.; Curran, D. P.; Geib, S. “Fluorous Synthesis of Hydantoin-, Piperidinedione-, and Benzodiazepinedione-Fused Tricyclic and Tetracyclic Ring Systems” Eur. J. Org. Chem. 2006, 2055-2059.

Fluorous Triphasic Reactions

  1. Curran DP, Werner S “Extractive phase vanishing reactions with dichloromethane, perfluorohexanes, and dibromoethane: Slow addition in a test tube” Org. Lett. 2004, 6, 1021-1024.
  2. Luo, Z.; Swaleh, S. M.; Theil, F.; Curran, D. P.   "Resolution of 1-(2-Naphthyl)ethanol by a Combination of an Enzyme-Catalyzed Kinetic Resolution with a Fluorous Triphasic Separative Reaction" Org. Lett. 2002, 4, 2585.
  3. I. Ryu, H. Matsubara, S. Yasuda, H. Nakamura, and D. P. Curran, "Phase-vanishing reactions that use fluorous media as a phase screen, facile, controlled bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide", J. Am Chem. Soc., in press.
  4. Z. Luo, S. M. Swaleh, F. Theil, and D. P. Curran, "Resolution of 1-(2-Naphthyl)ethanol by a combination of an enzyme-catalyzed kinetic resolution with a fluorous triphasic separative reaction", Org. Lett. 2002, 4, 2585. [Full Article - PDF]
  5. H. Nakamura, B. Linclau, D. P. Curran, "Fluorous triphasic reactions: Transportative deprotection of fluorous silyl ethers with concomitant purification", J. Am. Chem. Soc. 2001, 123, 10119-10120. [Full Article - PDF]
  6. I. Ryu, H. Matsubara, S. Yasuda, H. Nakamura, D. P. Curran, "Phase-vanishing reactions that use fluorous media as a phase screen. Facile, controlled bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide", J. Am. Chem. Soc. 2002, 124, 12946.

Issued Patents

  1. Zhang, W.; Luo, Z. Nagashima, T.; Chen, C. H.-T.; Yu, M. S. “Fluorous Tagging and Scavenging Reagents and Methods of Synthesis and Use Thereof” US7,060,850, 2006.
  2. B. Linclau, H. Nakamura, D. P. Curran, L. Sun, S. Weber, "Fluorous Triphase and Other Multiphase Systems", US6734318, 2004
  3. Q. Zhang, D. P. Curran, "Fluorous Phosphines and Phosphine Oxides", US6727390, 2004
  4. P. Wipf, J. Reeves, S. Roever, "Fluorous Tagging Compounds and Methods of Use Thereof", US6676539, 2004
  5. D. P. Curran, S. Hadida, M. Hoshino, A. Studer, S.-Y. Kim, P. Wipf, P. Jäger, "Fluorous Reaction and Separation Systems", US 6156896, 2000.
  6. D. P. Curran, S. Hadida, M. Hoshino, A. Studer, S.-Y. Kim, P. Wipf, P. Jäger, "Fluorous Reaction and Separation Systems", US 5859247, 1999.
  7. D. P. Curran, S. Hadida, M. Hoshino, A. Studer, "Fluorous Reaction Systems", US 5777121,1998.