Fluorous Literature Highlights for Small Molecule Synthesis

Review Articles
Fluorous Separation Media
Fluorous Protecting Groups and Tags
Fluorous Scavengers and Reagents
Fluorous Catalysts and Ligands
Fluorous Mixture Synthesis (FMS)
Microwave-Assisted Fluorous Synthesis
Fluorous Proteomics and Metabolomics

Review Articles

1. Zhang, W.; Curran, D. P. Synthetic Applications of Fluorous Solid-Phase Extraction (F-SPE). Tetrahedron 2006, 62, 11837–11865.
2. Zhang, W. Fluorous Technologies for Solution-Phase High-Throughput Organic Synthesis. Tetrahedron 2003, 59, 4475–4489.
3. Zhang, W. Fluorous Synthesis of Heterocyclic Systems. Chem. Rev. 2004, 104, 2531–2556.

Fluorous Separation Media

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. 96-Well Gravity Fluorous Solid-Phase Extraction for High-Throughput Purification. J. Comb. Chem. 2007, 9, 836–843.
3. Chu, Q.; Yu, M. S.; Curran, D. P. New Fluorous/Organic Biphasic Systems Achieved by Solvent Tuning. Tetrahedron 2007, 63, 9890–9895.
4. Yu, M. S.; Curran, D. P.; Nagashima, T. Increasing Fluorous Partition Coefficients by Solvent Tuning. Org. Lett. 2005, 7, 3677–3680.
5. Curran, D. P. Fluorous Reverse Phase Silica Gel. A New Tool for Preparative Separations in Synthetic Organic and Organofluorine Chemistry. Synlett 2001, 1488–1496.

Fluorous Protecting Groups and Tags

1. Dakas, P.-Y.; Barluenga, S.; Totzke, F.; Zirrgiebel, U.; Winssinger, N. Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors. Angew. Chem.; Int. Ed. 2007, 46, 6899–6902. (97071)
2. Wang, X.; Nelson, S. G.; Curran, D. P. The Azido Acid Approach to β-peptides: Parallel Synthesis of a Tri-β-peptide Library by Fluorous Tagging. Tetrahedron 2007, 63, 6141–6145. (97071)
3. McCairn, M. C.; Turner, M. L. Rapid Synthesis and Fluorous-phase Purification of α-perfluorohexyloligothiophenes. Tetrahedron Lett., 2007, 48, 1045–1047. (04636)
4. McAllister, L. A.; McCormick, R. A.; James, K. M.; Brand, S.; Willetts, N.; Procter, D. J. A Fluorous, Pummerer Cyclative-Capture Strategy for the Synthesis of N-Heterocycles. Chem.—Eur. J. 2007, 13, 1032–1046. (08686)
5. Schwinn, D.; Bannwarth, W. Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems. Helv. Chim. Acta 2002, 85, 255. (14944)
6. Curran, D. P.; Amatore, M.; Campbell, M.; Go, E.; Guthrie, D.; Luo, Z. Synthesis and Reactions of Fluorous Carbobenzyloxy (FCbz) Derivatives of α-amino Acids. J. Org. Chem. 2003, 68, 4643. (14944)
7. Palmacci, E. R.; Hewitt, M. C.; Seeberger, P. H. Cap-Tag-Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis. Angew. Chem., Int. Ed. 2001, 40, 4433–4437. (04537)
8. Manzoni, L. Rapid Synthesis of Oligosaccharides using an Anomeric Fluorous Silyl Protecting Group. Chem. Commun. 2003, 2930. (04537)
9. Trabanco, A. A.; Vega, J. A.; Fernández, M. A. Fluorous-Tagged Carbamates for the Pd-Catalyzed Amination of Aryl Halides. J. Org. Chem. 2007, 72, 8146. (55118)
10. Mamidyala, S. K.; Firestine, S. M. Fluorous Synthesis of Minor Groove Binding Agents Related to Distamycin. Tetrahedron Lett. 2006, 47, 7431. (55118)
11. Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D. P. Fluorous Boc (FBoc) Carbamates: New Amine Protecting Groups for use in Fluorous Synthesis. J. Org. Chem. 2001, 66, 4261–4266. (55118)
12. Chen, C. H.-T.; Zhang, W. FluoMar, a Fluorous Version of the Marshall Resin for Solution-Phase Library Synthesis. Org. Lett. 2003, 5, 1015. (40829)

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Fluorous Scavengers and Reagents

1. Baslé, E.; Jean, M.; Gouault, N.; Renault, J.; Uriac, P. Fluorous Scavenger for Parallel Preparation of Tertiary Sulfonamides Leading to Secondary Amines. Tetrahedron Lett. 2007, 48, 8138. (68794)
2. Lindsley, C. W.; Zhao, Z.; Leister, W. H. Fluorous-Tethered Quenching Reagents for Solution Phase Parallel Synthesis. Tetrahedron Lett. 2002, 43, 4225. (08686)
3. Zhang, W.; Curran, D. P.; Chen, C. H.-T. Use of Fluorous Silica Gel to Separate Fluorous Thiol Quenching Derivatives in Solution-Phase Parallel Synthesis. Tetrahedron 2002, 58, 3871–75. (08686)
4. Dakas, P.-Y.; Barluenga, S.; Totzke, F.; Zirrgiebel, U.; Winssinger, N. Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors. Angew. Chem., Int. Ed. 2007, 46, 6899–6902. (68333, 07026)
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. (68333, 07026)
6. Curran, D. P.; Bajpai, R.; Sanger, E. Purification of Fluorous Mitsunobu Reactions by Liquid-Liquid Extraction Adv. Synth. Catal. 2006, 348, 1621–1624. (68333, 19971)
7. Gerard, B.; Cencic, R.; Pelletier, J.; Porco, J. A., Jr. Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol. Angew. Chem., Int. Ed. 2007, 46, 7831. (07026)
8. Bucher, B.; Curran, D. P. Selective Sulfonylation of 1,2-diols and Derivatives Catalyzed by a Recoverable Fluorous Tin Oxide. Tetrahedron Lett. 2000, 41, 9617–9621. (43482)
9. Ryu, I.; Niguma, T.; Minakata, S.; Komatsyu, M.; Luo, Z. Y.; Curran, D. P. Radical Carbonylations with Fluorous Allyltin Reagents. Tetrahedron Lett. 1999, 40, 2367–2370. (039045)
10. 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. J. Am. Chem. Soc. 2006, 128, 3536. (039049)

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Fluorous Catalysts and Ligands

1. Kirillov, E.; Lavanant, L.; Thomas, C.; Roisnel, T.; Chi, Y.; Carpentier, J.-F. Chiral Fluorous Dialkoxy-Diamino Zirconium Complexes: Synthesis and Use in Stereospecific Polymerization of 1-Hexene. Chem.—Eur. J. 2007, 13, 923–935.
2. Yi, W.-B.; Cai, C.; Wang, X. A Palladium/Perfluoroalkylated Pyridine Catalyst for Sonogashira Reaction of Aryl Bromides and Chlorides in a Fluorous Biphasic System. Eur. J. Org. Chem. 2007, 3445–3448.
3. Yi, W.-B.; Cai, C.; Wang, X. A Novel Fluorous Palladium Catalyst for Heck Reaction in a Fluorous Biphase System (FBS). J. Mol. Catal. A: Chem. 2007, 274, 68–71.
4. Lu, N.; Lin, Y.-C.; Chen, J.-Y.; Fan, C.-W.; Liu, L.-K. New Bis(fluoro-ponytailed) Bipyridine Ligands for Pd-catalyzed Heck Reactions under Fluorous Biphasic Catalysis Condition. Tetrahedron 2007, 63, 2019–2023.
5. Moura-Letts, G.; Curran, D. P. Selective Synthesis of (2Z,4E)-Dienyl Esters by Ene-Diene Cross Metathesis. Org. Lett. 2007, 9, 5–8.
6. da Costa, R. C.; Hampel, F.; Gladysz, J. A. Crystal Structure of an Unusual bis(fluorous phosphine)ruthenium(III) Complex Derived from a Fluorous Grubbs’ Catalyst. Polyhedron 2007, 26, 581–588.
7. da Costa, R. C.; Gladysz, J. A. Syntheses and Reactivity of Analogues of Grubbs' Second Generation Metathesis Satalyst with Fluorous Phosphines: A New Phase-Transfer Strategy for Catalyst Activation. Adv. Synth. Catal. 2007, 349, 243–254.
8. Horn, J.; Bannwarth, W. Repetitive Application of a Fluorous Chiral BINAP–Ru Complex in the Asymmetric Hydrogenation of Olefins. Eur. J. Org. Chem. 2007, 2058–2063.

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Fluorous Mixture Synthesis (FMS)

1. Crich, D.; Grant, D.; Bowers, A. A. Heterobivalent Library Expansion by "Living Radical" Processes: Thiocarbonyl Addition/Elimination, and Nitroxide-Based Reactions with Fluorous Deconvolution. J. Am. Chem. Soc. 2007, 129, 12106.
2. Tonoi, T.; Mikami, K. Fluorous "Racemic" Mixture Synthesis: Simultaneous Strategy for Demixing and Enantioseparation of Racemic Fluorous-Tagged Products. Eur. J. Org. Chem. 2007, 11, 1730–1733.
3. Fukui, Y.; Brückner, A. M.; Shin, Y.; Balachandran, R.; Day, B. W.; Curran, D. P. Fluorous Mixture Synthesis of (-)-Dictyostatin and Three Stereoisomers. Org. Lett. 2006, 8, 301–304.
4. Gudipati, V.; Curran, D. P.; Wilcox, C. S. 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.
5. Curran, D. P.; Oderaotoshi, Y. 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.
6. Zhang, W.; Luo, Z.; Chen, C. H. T.; Curran, D. P. Solution-Phase Preparation of a 560-Compound Library of Individual Pure Mappicine Analogues by Fluorous Mixture Synthesis. J. Am. Chem. Soc. 2002, 124, 10443.

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Microwave-Assisted Fluorous Synthesis

1. Zhang, W. Microwave-Enhanced High-Speed Fluorous Synthesis. In Microwave Methods in Organic Synthesis; Topics Current Chemistry; Larhed, M.; Olofsson, K., Eds.; Springer: 2006; Vol. 266, pp 145–166.
2. 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.
3. Zhang, W.; Tempest, P. Highly Efficient Microwave-Assisted Fluorous Ugi and Post-Condensation Reactions for Benzimidazoles and Quinoxalinones. Tetrahedron Lett. 2004, 45, 6757–6760. (55118)

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Fluorous Proteomics and Metabolomics

1. Brittain, S. M.; Ficarro, S. B.; Brock, A.; Peters, E. C. Enrichment and Analysis of Peptide Subsets using Fluorous Affinity Tags and Mass Spectrometry. Nat. Biotechnol. 2005, 23, 463.
2. Go, E. P.; Uritboonthai, W.; Apon, J. V.; Trauger, S. A.; Nordstrom, A.; O'Maille, G.; Brittain, S. M.; Peters, E. C.; Siuzdak, G. Selective Metabolite and Peptide Capture/Mass Detection using Fluorous Affinity Tags. J. Proteome Res. 2007, 6, (4), 1492–1499.

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