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Highlights of Recent Fluorous Research & References from 2006 to present

 

Reviews and a special issue of journal.  In an article published in Aldrichimica Acta (2006, 39, 3), Prof. Curran highlighted the progress of “light fluorous” chemistry including the utilities of fluorous reagents, reactants, catalysts, scavengers for small molecule and biomolecule synthesis.  The synthetic utility of fluorous solid-phase extraction (F-SPE) has been reviewed in a Tetrahedron Report by Zhang and Curran (Tetrahedron 2006 62, 11837).  The combination of microwave and fluorous technologies to increase reaction speed and facilitate product separations has also been reviewed in an article published in Topics Curr. Chem. (2006, 266, 145).  Prof. Kumer and coworkers summarized the progress of fluorous technology for chemical biology applications (Curr. Opin. Chem. Bio. 2006, 10, 1).  A special issue of “Fluorous synthesis” featured 16 articles has been published in QSAR & Combinatorial Science (2006, 25, 679-768).

 

Fluorous Separation Techniques:  Follow up on the development of 24-well plate-to-plate F-SPE for parallel purifications (J. Comb. Chem. 2005, 7, 893), FTI recently reported an automated SPE technique using RapidTrace workstation to increase the throughput of F-SPE.  The system has the capability to conduct up to one hundred SPEs in 1-2 h.  In a collaboration work of FTI and Takeda-San Diego, a MS-triggered 4-column parallel F-HPLC method has been developed to analyze samples in FMS. Its potential for prep-scale high-throughput parallel demixing to increase the efficiency of FMS has also been demonstrated (J. Comb. Chem.  2006, 8, 687).

 

Biphasic Liquid-Liquid Extraction Systems: The Otera group published a paper on fluorophilicity switch by solvation (J. Am. Chem Soc. 2006, 128, 4182).  The fluorous distannoxanes as the hydrates were found not soluble in both fluorous solvent FC-72 and in organic solvent MeCN. However, the fluorous distannoxanes were well dissolved a biphasic system containing MeCN and FC-72, and in favor of the FC-72 layer.  The fluorous compounds were fluorophobic when solvated by the water molecules, but turned to fluorophilic when solvated with MeCN.  The Curran group developed a biphasic solvent system (2:1 HFE-7100/FC-72 and DMF/10% water) for separation of reaction mixtures generated from Mitsunobu reactions using fluorous diazodicarboxlate and phosphine (Adv. Synth. Catal. 2006, 348, 1621).

 

Fluorous Mixture Synthesis (FMS):  FMS is a highly efficient solution-phase technology for library synthesis.  The Wilcox and Curran groups introduced a “double-tagging” strategy by using oligoethylene glycol (OEG) tags for polarity-controlled separation and using fluorous tags for fluorophilicity-controlled separation to further enhance the capability of FMS (J. Org. Chem. 2006, 71, 3599).  This new protocol has been demonstrated in the synthesis of stereoisomers of the hydroxybutenolide fragmsent of Murisolin.  Other works on FMS include structure assignment of Lagunapyrone B (J. Ame. Chem Soc. 2006, 128, 14200), synthesis of stereoisomers of (-)-dictyostatin (Org. Lett. 2006, 8, 301), and diversity-oriented synthesis (DOS) of novel heterocyclic compound libraries (J. Comb. Chem.  2006, 8, 687).

 

Fluorous Displaceable Tags and Protecting groups: The Valliant group introduced a new strategy for synthesis and purification of "precursor-free" radiopharmaceutical imaging agents (J. Am. Chem. Soc. 2006, 128, 3536).  In the multiple-step synthesis, intermediates containing the fluorous tin tag were readily purified by F-LLE) and the final 125I labeled products were removed by F-SPE to give >98% purities.  The Gouault group employed a fluorous acrylate in the synthesis of substituted R-methylene-a-lactone library (J. Comb. Chem. 2006, 8, 643).  The Takeuchi group developed N,N-bis(perfluoroalkyl)thiocarbamoyl chlorides (F-DMTC-Cls) for alcohol group protection (Tetrahedron Lett. 2006, 47, 6309) and tris(peruorodecyl) silylethoxylcarbonyl (F-Teoc) for amino group protection (Tetrahedron Lett. 2006, 47, 239). The Fustero group introduced a fluorous (trimethylsilyl)ethanol for protection of carboxylic acids.  The Kondo group employed sulfonamide type fluorous protecting group in the synthesis of biologically-attractive bisindole derivatives (Chem. Commun. 2006, 891).

 

Fluorous Reagents and Scavengers. The Soós and Dembinski groups developed fluorous Lawesson’s reagent to simplify the byproduct purification the thionation reaction of carbonyl (Org. Lett. 2006, 8, 1093) as well as preparation of sulfur-containing heterocyclic compounds (Org. Lett. 2006, 8, 1625).  Fluorous dichlorotriazines have been employed as amide coupling agents to produce two equiv of products (QSAR Comb. Sci. 2006, 724).  The same reagents can also be used as scavengers to remove amines and thiols from the reaction mixture (QSAR Comb. Sci. 2006, 728).

 

Fluorous Organocatalysts: The Wang group developed a fluorous (S)-pyrrolidine sulfonamide organocatalyst for enantio- and diastereoselective Michael addition reactions (Org Lett. 2006, 8, 3077). The organocatalyst is recovered by F-SPE and can be reused up to 6 cycles without a significant loss of catalytic activity and stereoselectivity.  FTI reported the synthesis and application of fluorous imidazolidinone catalyst for asymmetric Diels-Alder reactions (Tetrahedron Lett. 2006, 47, 9287).

 

Fluorous Nanotechnology: The Fujita group reported the synthesis of a fluorous droplet containing 24 perfluoroalkyl chains, 12 palladium ions and 24 bridging ligands (Science 2006, 313, 1273).  Perfluoroalkanes can dissolve in this well-defined fluorous cage, and their solubility can be finely controlled by tuning the length of perfluoroalkyl chains tethered to the shell.  The Rao group employed fluorous technologies to synthesize gold and CdSe nanoparticles, single-walled carbon nanotubes, and ZnO nanorods to study the optical and other properties of these nanomaterials (J. Phys. Chem. B 2006, 110, 20752).

 

 

Updated References

 

Fluorous Small Molecule Applications 

  1. Curran, D. P.; Zhang, Q.; Richard, C.; Lu, H.; Gudipati, V.; Wilcox, C. S. "Total Synthesis of a 28-Member Stereoisomer Library of Murisolins." Journal of the American Chemical Society 2006, 128, 9561-9573.
  2. Donovan, A.; Forbes, J.; Dorff, P.; Schaffer, P.; Babich, J.; Valliant, J. F. "A New Strategy for Preparing Molecular Imaging and Therapy Agents Using Fluorine-Rich (Fluorous) Soluble Supports." Journal of the American Chemical Society 2006, 128, 3536-3537.
  3. Hao, X.; Hoshi, N. "Facile and recyclable method for the prins reaction using hafnium(IV) bis(perfluorooctanesulfonyl)amides in fluorous biphase system." Chemistry Letters 2006, 35, 1102-1103.
  4. Hao, X.; Yoshida, A.; Nishikido, J. "Metal bis(perfluorooctanesulfonyl)amides as highly efficient Lewis acid catalysts for fluorous biphase organic reactions." Journal of Fluorine Chemistry 2006, 127, 193-199.
  5. Yi, W.-B.; Cai, C. "Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media." Journal of Fluorine Chemistry 2006, 127, 1515-1521.
  6. Yoshida, A.; Hao, X.; Yamazaki, O.; Nishikido, J. "Development of fluorous Lewis acid-catalyzed reactions." Molecules 2006, 11, 627-640.
  7. Michalek, F.; Bannwarth, W. "Application of a Grubbs-Hoveyda metathesis catalyst noncovalently immobilized by fluorous-fluorous interactions." Helvetica Chimica Acta 2006, 89, 1030-1037.
  8. Correa da Costa, R.; Gladysz, J. A. "Fluorous phase-transfer activation of catalysts: application of a new rate-enhancement strategy to alkene metathesis."Chemical Communications (Cambridge, United Kingdom) 2006, 2619-2621.
  9. Zu, L.; Li, H.; Wang, J.; Yu, X.; Wang, W. "Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether." Tetrahedron Letters 2006, 47, 5131-5134.
  10. Zu, L.; Wang, J.; Li, H.; Wang, W. "A Recyclable Fluorous (S)-Pyrrolidine Sulfonamide Promoted Direct, Highly Enantioselective Michael Addition of Ketones and Aldehydes to Nitroolefins in Water." Organic Letters 2006, 8, 3077-3079.
  11. Chu, Q.; Zhang, W.; Curran, D. P. "A recyclable fluorous organocatalyst for Diels-Alder reactions." Tetrahedron Letters 2006, 47, 9287-9290.
  12. Bayardon, J.; Holczknecht, O.; Pozzi, G.; Sinou, D. ). "Asymmetric cyclopropanation catalyzed by fluorous bis(oxazolines)-copper complexes." Tetrahedron: Asymmetry 2006, 17, 1568-1572.
  13. de Castries, A.; Magnier, E.; Monmotton, S.; Fensterbank, H.; Larpent, C. "An expedient synthesis of perfluorinated tetraazamacrocycles: new ligands for copper-catalyzed oxidation under fluorous biphasic conditions." European Journal of Organic Chemistry 2006, 4685-4692.
  14. de Pater, J. J. M.; Deelman, B.-J.; Elsevier, C. J.; van Koten, G. "Lightly fluorous [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2] in the methoxycarbonylation of styrene: Formation, performance and stability of the catalyst system." Journal of Molecular Catalysis A: Chemical 2006, 258, 334-340.
  15. Gheorghe, A.; Cuevas-Yanez, E.; Horn, J.; Bannwarth, W.; Narsaiah, B.; Reiser, O. "A facile strategy to a new fluorous-tagged, immobilized TEMPO catalyst using a click reaction, and its catalytic activity."Synlett 2006, 2767-2770.
  16. Hope, E. G.; Sherrington, J.; Stuart, A. M. "Supported fluorous phase catalysis on PTFE, fluoroalkylated micro- and meso-porous silica."  Advanced Synthesis & Catalysis 2006, 348, 1635-1639.
  17. Huang, Y.-Y.; He, Y.-M.; Zhou, H.-F.; Wu, L.; Li, B.-L.; Fan, Q.-H. "Thermomorphic System with Non-Fluorous Phase-Tagged Ru(BINAP) Catalyst: Facile Liquid/Solid Catalyst Separation and Application in Asymmetric Hydrogenation." Journal of Organic Chemistry 2006, 71, 2874-2877.
  18. Pedros, M. G.; Masdeu-Bulto, A. M.; Bayardon, J.; Sinou, D. "Hydroformylation of Alkenes with Rhodium Catalyst in Supercritical Carbon Dioxide." Catalysis Letters 2006, 107, 205-208.
  19. Tsang, S. C.; Zhu, J.; Yu, K. M. K. "A New Oxidation Catalyst System using Fluorous Cobalt(II) Species in Water-supercritical Carbon dioxide (C-H free environment)." Catalysis Letters 2006, 106, 123-126.
  20. Yi, W.-B.; Cai, C. "Cobalt(II) Perfluorooctane Sulfonate Catalyzed Highly Efficient Aerobic Oxidation of Alcohols in Fluorous Biphasic Systems." Australian Journal of Chemistry 2006, 59, 349-353.
  21. Zhang, W.; Lu, Y. "Automation of Fluorous Solid-Phase Extraction for Parallel Synthesis." Journal of Combinatorial Chemistry 2006, 8, 890-896.
  22. 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."Journal of Combinatorial Chemistry 2006, 8, 687-695.
  23. Le Lamer, A.-C.; Gouault, N.; David, M.; Boustie, J.; Uriac, P. "Method for the Parallel Synthesis of a-Methylene-g-lactones from a Fluorous Acrylate."Journal of Combinatorial Chemistry 2006, 8, 643-645.
  24. Kojima, M.; Nakamura, Y.; Ishikawa, T.; Takeuchi, S. "Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols."Tetrahedron Letters 2006, 47, 6309-6314.
  25. Nakamura, Y.; Okumura, K.; Kojima, M.; Takeuchi, S. "An expeditious synthesis of bistratamide H using a new fluorous protecting group."Tetrahedron Letters 2006, 47, 239-243.
  26. Zhang, W.; Nagashima, T. "Palladium-catalyzed Buchwald-Hartwig type amination of fluorous arylsulfonates."Journal of Fluorine Chemistry 2006, 127, 588-591.
  27. Kaleta, Z.; Makowski, B. T.; Soos, T.; Dembinski, R. "Thionation Using Fluorous Lawesson's Reagent." Organic Letters 2006, 8, 1625-1628.
  28. Kaleta, Z.; Tarkanyi, G.; Goemoery, A.; Kalman, F.; Nagy, T.; Soos, T. "Synthesis and Application of a Fluorous Lawesson's Reagent: Convenient Chromatography-Free Product Purification." Organic Letters 2006, 8, 1093-1095.

 

Fluorous Proteomics:

  1. Go, E.P.; Uritboonthai, W.; Apon, J. V.; Trauger, S. A.; Nordstrom, A.; O’naille, G.; Brittai, S. M.; Peters, E. C.; Siuzadak, G. “Fluorous affinity tags for selective metabolite and peptide capture and mass detection” J. proteomics” Journal of Proteome Research  2007, 6,1492-1499.
  2. Scott M. Brittain, Scott B. Ficarro, Ansgar Brock, Eric C. Peters “Fluorous Proteomics: Enrichment and Analysis of Peptide Subsets using Fluorous Affinity Tags and Mass Spectrometry” Nat. Biotech. 2005, 23, 463-468.

 

Fluorous Microarray:

  1. Arturo J. Vegas, James E. Bradner, Weiping Tang, Olivia M. McPherson, Edward F. Greenberg, Angela N. Koehler, Stuart L. Schreiber “Fluorous-Based Small-Molecule Microarrays for the Discovery of Histone Deacetylase Inhibitors” Angewandte Chemie International Edition 2007, asap.
  2. Sreeman K. Mamidyala, Kwang-Seuk Ko, Firoz A. Jaipuri, Gisun Park and Nicola L. Pohl “Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays”J. F. Chem. 2006, 127, 571-579.
  3. Pohl, N. L. "Fluorous-based microarrays for probing carbohydrate-protein recognition."Abstracts of Papers, 231st ACS National Meeting, Atlanta, GA, United States, March 26-30, 2006 2006, CARB-025.
  4. Pohl, N. L. "Carbohydrate microarrays and automated fluorous-phase oligosaccharide synthesis." Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006 2006, CARB-028.
  5. Kwang-Seuk Ko, Firoz A. Jaipuri, and Nicola L. Pohl “Fluorous-Based Carbohydrate Microarrays” J. Am. Chem. Soc. 2005, 127, 13162-13163.

 

 

Fluorous Biomolecule Chemistry: 

  1. Floegel, O.; Codee, J. D. C.; Seebach, D.; Seeberger, P. H. "Microreactor synthesis of ?-peptides."Angewandte Chemie, International Edition 2006, 45, 7000-7003.
  2. Mamidyala, S. K.; Firestine, S. M. "Fluorous synthesis of minor groove binding agents related to distamycin."Tetrahedron Letters 2006, 47, 7431-7434.
  3. Glen Research Report:  http://www.glenres.com/index.html?/GlenReports/GR18-16.html
  4. Mishra, R.; Mishra, S.; Misra, K. "Synthesis and application of fluorous-tagged oligonucleotides." Chemistry Letters 2006, 35, 1184-1185.
  5. Fustero, S.; Garcia Sancho, A.; Chiva, G.; Sanz-Cervera, J. F.; Del Pozo, C.; Acena, J. L. "Fluorous (trimethylsilyl)ethanol: a new reagent for carboxylic acid tagging and protection in peptide synthesis." Journal of Organic Chemistry 2006, 71, 3299-3302.
  6. Lee, H.-Y.; Lee, K.-H.; Al-Hashimi, H. M.; Marsh, E. N. G. ). "Modulating Protein Structure with Fluorous Amino Acids: Increased Stability and Native-like Structure Conferred on a 4-Helix Bundle Protein by Hexafluoroleucine."Journal of the American Chemical Society 2006, 128, 337-343.
  7. Manzoni, L.; Castelli, R. "Froc: A New Fluorous Protective Group for Peptide and Oligosaccharide Synthesis." Organic Letters 2006, 8, 955-957.
  8. Matsugi, M.; Yamanaka, K.; Inomata, I.; Takekoshi, N.; Hasegawa, M.; Curran, D. P. "Synthesis of fluorous-FMOC reagents and purification of protected dipeptides with fluorous solid phase extraction." QSAR & Combinatorial Science 2006, 25, 713-715.
  9. Mizuno, M.; Goto, K.; Miura, T. "Synthesis of peptides by using a recyclable fluorous tag." Peptide Science 2006, 42nd, 119-122.
  10. Mizuno, M.; Goto, K.; Miura, T.; Inazu, T. "Rapid oligosaccharide and peptide syntheses on a recyclable fluorous support."QSAR & Combinatorial Science 2006, 25, 742-752.
  11. Mizuno, M.; Matsumoto, H.; Goto, K.; Hamasaki, K. "Synthesis of aminoglycoside derivatives on a Cbz-type heavy fluorous tag." Tetrahedron Letters 2006, 47, 8831-8835.
  12. Montanari, V.; Kumar, K. "Enabling routine fluorous capping in solid phase peptide synthesis." Journal of Fluorine Chemistry 2006, 127, 565-570.
  13. Montanari, V.; Kumar, K. "A fluorous capping strategy for fmoc-based automated and manual solid-phase peptide synthesis." European Journal of Organic Chemistry 2006, 874-877.
  14. Nakamura, Y.; Okumura, K.; Kojima, M.; Takeuchi, S. "An expeditious synthesis of bistratamide H using a new fluorous protecting group."Tetrahedron Letters 2006, 47, 239-243.
  15. Ueki, M.; Tojo, K.-i.; Kishina, T.; Kobata, C. "Preparation of fluorous-tagged active ester for rapid peptide synthesis."Peptide Science 2006, 42nd, 123-126.
  16. Wang, X.; Curran, D. P. "Fluorous Parallel Synthesis of 3*3*3 -Peptide Library." Abstracts, 35th Northeast Regional Meeting of the American Chemical Society, Binghamton, NY, United States, October 5-7 2006, NRM-539.
  17. Ikeda, K.; Mori, H.; Sato, M. "Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor." Chemical Communications (Cambridge, United Kingdom) 2006, 3093-3094.
  18. Kasuya, M. C. Z.; Murozuka, Y.; Hatanaka, K. "Production of oligosaccharides by using cells with a view of constructing the functional nano-structure." Nanotechnology in Carbohydrate Chemistry 2006, 23-42.
  19. Mamidyala, S. K.; Ko, K.-S.; Jaipuri, F. A.; Park, G.; Pohl, N. L. "Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays." Journal of Fluorine Chemistry 2006, 127, 571-579.
  20. Manzoni, L.; Castelli, R. "Froc: A New Fluorous Protective Group for Peptide and Oligosaccharide Synthesis."Organic Letters 2006, 8, 955-957.
  21. Park, G.; Pohl, N. L. "Synthesis of biosynthetic precursors of anthrax- and cholera-related antigenic carbohydrates." Abstracts of Papers, 231st ACS National Meeting, Atlanta, GA, United States, March 26-30, 2006 2006, CARB-081.

 

Fluorous Micro and Nano Applications: 

  1. Shoichi Shimizu, Toshiyuki Kiuchi, and Na Pan “A “Teflon-Footed” Resorcinarene: A Hexameric Capsule in Fluorous Solvents and Fluorophobic Effects on Molecular Encapsulation” Angew. Chem. Int. Ed 2007 article asap.
  2. Jason G. Kralj, Hemantkumar R. Sahoo and Klavs F. Jensen “Integrated continuous microfluidic liquid–liquid extraction” Lab Chip, 2007, 7, 256–263.
  3. Guoqing Hu, Jacky S.H. Lee, Dongqing Li “A microfluidic fluorous solid-phase extraction chip for purification of amino acids”Journal of Colloid and Interface Science 2006, 301, 697–702.
  4. Oliver Flogel, Jeroen D. C. Codee, Dieter Seebach, and Peter H. Seeberger “Microreactor Synthesis of ?-Peptides” Angew. Chem. Int. Ed. 2006, 45, 7000-7003.
  5. Mikami, K.; Yamanaka, M.; Islam, M. N.; Tonoi, T.; Itoh, Y.; Shinoda, M.; Kudo, K. "Nanoflow microreactor for dramatic increase not only in reactivity but also in selectivity: Baeyer-Villiger oxidation by aqueous hydrogen peroxide using lowest concentration of a fluorous lanthanide catalyst." Journal of Fluorine Chemistry 2006, 127, 592-596.
  6. Sato, S.; Iida, J.; Suzuki, K.; Kawano, M.; Ozeki, T.; Fujita, M. "Fluorous Nanodroplets Structurally Confined in an Organopalladium Sphere."Science (Washington, DC, United States) 2006, 313, 1273-1276.
  7. Voggu, R.; Biswas, K.; Govindaraj, A.; Rao, C. N. R. "Use of Fluorous Chemistry in the Solubilization and Phase Transfer of Nanocrystals, Nanorods, and Nanotubes." Journal of Physical Chemistry B 2006, 110, 20752-20755.
  8. Hu, G.; Lee, J. S. H.; Li, D. "A microfluidic fluorous solid-phase extraction chip for purification of amino acids." Journal of Colloid and Interface Science 2006, 301, 697-702.
  9. Guo, R.; Ramjee, B.; Mills, A.; Murray, R. W. "Synthesis and characterization of perfluorinated gold nanoparticles. "Abstracts of Papers, 231st ACS National Meeting, Atlanta, GA, United States, March 26-30, 2006 2006, COLL-245.
  10. Kasuya, M. C. Z.; Murozuka, Y.; Hatanaka, K. "Production of oligosaccharides by using cells with a view of constructing the functional nano-structure." Nanotechnology in Carbohydrate Chemistry 2006, 23-42.
  11. Krafft, M. P. "Highly fluorinated compounds induce phase separation in, and nanostructuration of liquid media. Possible impact on, and use in chemical reactivity control." Journal of Polymer Science, Part A: Polymer Chemistry 2006, 44, 4251-4258.
  12. Lantos, D.; Contel, M.; Larrea, A.; Szabo, D.; Horvath, I. T. "Fluorous phosphine-assisted recycling of gold catalysts for hydrosilylation of aldehydes." QSAR & Combinatorial Science 2006, 25, 719-722.
  13. Serra-Muns, A.; Soler, R.; Badetti, E.; de Mendoza, P.; Moreno-Manas, M.; Pleixats, R.; Sebastian, R. M.; Vallribera, A. "15-Membered triolefinic macrocycles as stabilizers of palladium(0) nanoparticles." New Journal of Chemistry 2006, 30, 1584-1594.
  14. Floegel, O.; Codee, J. D. C.; Seebach, D.; Seeberger, P. H. "Microreactor synthesis of ?-peptides."Angewandte Chemie, International Edition 2006, 45, 7000-7003.

Fluorous Reviews 

  1. Curran, D. P. "Organic synthesis with light-fluorous reagents, reactants, catalysts, and scavengers." Aldrichimica Acta 2006, 39, 3-9.
  2. Dandapani, S. "Recent applications of fluorous separation methods in organic and bioorganic chemistry." QSAR & Combinatorial Science 2006, 25, 681-688.
  3. Yoshida, A.; Hao, X.; Yamazaki, O.; Nishikido, J. "Development of fluorous Lewis acid-catalyzed reactions." Molecules 2006, 11, 627-640.
  4. Zhang, W.; Curran, D. P. "Synthetic applications of fluorous solid-phase extraction (F-SPE)." Tetrahedron 2006, 62, 11837-11865.
  5. Zhang, W. "Microwave-Enhanced High Speed Fluorous Synthesis." Topics in Current Chemistry 2006, 266.
  6. Yoder, N. C.; Yueksel, D.; Dafik, L.; Kumar, K. "Bioorthogonal noncovalent chemistry: fluorous phases in chemical biology." Current Opinion in Chemical Biology 2006, 10, 576-583.