Highlights of 2007 Fluorous Publications for Small Molecule Synthesis

Review Articles:

1. Zhang, W. “Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds” Comb. Chem. High Throughput Screening 2007, 10, 219-229.

Fluorous Separation Techniques:

1. Zhang, W.; Lu, Y “96-Well Gravity Fluorous Solid-Phase Extraction for High-Throughput Purification” J. Comb. Chem. 2007, 9, 836-843.
2. Gifty Osei-Prempeh, Hans-Joachim Lehmler, Stephen E. Rankin and Barbara L.Knutson “Synthesis of Fluoro-Functionalized Mesoporous Silica and Application to Fluorophilic Separations” Industrial & Engineering Chemistry Research 2007, asap.
3. Qianli Chu, Marvin S. Yu, and Dennis P. Curran “New fluorous/organic biphasic systems achieved by solvent tuning” Tetrahedron 2007, 63, 9890-9895.
4. Tatsuo Maruyama, Kazunori Nakashima, Fukiko Kubota, Masahiro Goto “Perfluorocarbon-Based Liquid–Liquid Extraction for Separation of Transition Metal Ions” Analytical Sciences 2007, 23, 763-765.

Fluorous Reagents:

1. Masato Matsugi, Masakazu Hasegawa, Daisuke Sadachika, Sachina Okamoto, Mami Tomioka, Yoshimi Ikeya "Preparation and condensation reactions of a new light-fluorous Mukaiyama reagent: Reliable purification with fluorous solid phase extraction for esters and amides" Tetrahedron Lett. 2007, asap.
2. László Mercs, Gianluca Pozzi and Silvio Quici “Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates” Tetrahedron Letters 2007, 48, 3053-3056.
3. Cyrous O. Kangani, Billy W. Day and David E. Kelley “Direct, facile synthesis of acyl azides and nitriles from carboxylic acids using bis(2-methoxyethyl)aminosulfur tri.uoride” Tetrahedron Letters 2007, 48, 5933–5937.
4. del Pozo, C.; Keller, A. I.; Nagashima, T.; Curran, D. P. “Amide Bond Formation with a New Fluorous Carbodiimide: Separation by Reverse Fluorous Solid-Phase Extraction” Org. Lett, 2007, 9, in press.
5. Hiroshi Matsubara Louis Maeda, Hiroyuki Sugiyama, Ilhyong Ryu “Chiral and Achiral Lithium Amides Having a Fluorous Ponytail: Preparation and Evaluation as a Recycling Reagent for Lithium Enolate Generation” Synthesis 2007, 2901–2912.
6. Pierre-Yves Dakas, Sofia Barluenga, Frank Totzke, Ute Zirrgiebel, Nicolas Winssinger “Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors” Angewandte Chemie International Edition 2007, 46, 6899-6902.
7. Baudouin Gerard, Regina Cencic, Jerry Pelletier, and John A. Porco, Jr. “Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol” Angewandte Chemie International Edition 2007, asap

Fluorous Linkers (Protecting Groups and Tags):

1. Mark C. McCairn and Michael L. Turner “Rapid synthesis and fluorous-phase purification of α-perfluorohexyloligothiophenes” Tetrahedron Letters 2007, 48, 1045-1047.
2. Laura A. McAllister, Rosemary A. McCormick, Karen M. James, Stephen Brand, Nigel Willetts, David J. Procter “A Fluorous, Pummerer Cyclative-Capture Strategy for the Synthesis of N-Heterocycles” Chemistry - A European Journal 2007, 13, 1032-1046.
3. Zhong-Xing Jiang and Y. Bruce Yu “The Synthesis of a Geminally Perfluoro-tert-butylated ‚-Amino Acid and its Protected Forms as a Potential Pharmacokinetic Modulator and Reporter for Peptide-Based Pharmaceuticals” J. Org. Chem. 2007, 72, 1464-1467.
4. Xiao Wang, Scott G. Nelson and Dennis P. Curran “The azido acid approach to β-peptides: parallel synthesis of a tri-β-peptide library by fluorous tagging “Tetrahedron 2007, 63, 6141-6145.
5. Masaru Kojima, Yutaka Nakamura and Seiji Takeuchi “A practical fluorous benzylidene acetal protecting group for a quick synthesis of disaccharides” Tetrahedron Letters 2007, 48, 4431-4436.
6. David Horhant, Anne-Cécile Le Lamer, Joël Boustie, Philippe Uriac and Nicolas Gouault “Separation of a Mixture of Paraconic Acids from Cetraria islandica (L.) Ach. Employing a Fluorous Tag – Catch and Release Strategy” Tetrahedron Letters 2007 asap.
7. Spivey, Alan C.; Tseng, Chih-Chung; Hannah, Joseph P.; Gripton, Christopher J. G.; de Fraine, Paul; Parr, Nigel J.; Scicinski, Jan J. “Light-fluorous safety-catch arylgermanes - exceptionally robust, photochemically activated precursors for biaryl synthesis by Pd(0) catalysed cross-coupling” Chemical Communications 2007, 2926-2928.
8. “The development of a ‘safety-catch’ arylgermane for biaryl synthesis by palladium-catalysed germyl-Stille cross-coupling” Appl. Organometal. Chem. 2007, 21: 572–589.
9. Pierre-Yves Dakas, Sofia Barluenga, Frank Totzke, Ute Zirrgiebel, Nicolas Winssinger “Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors” Angewandte Chemie International Edition 2007, 46, 6899-6902.
10. Andrés A. Trabanco, Juan A. Vega and M. Alejandro Fernández “Fluorous Tagged Carbamates for the Pd-Catalyzed amination of Aryl Halides” J. Org. Chem. 2007, asap.
11. Hiroshi Naka, Yusuke Akagi, Kyoko Yamada, Tatsushi Imahori, Takahiro Kasahara, and Yoshinori Kondo “Fluorous Synthesis of Yuehchukene by α-Lithiation of Perfluoroalkyl-Tagged 1-(Arylsulfonyl)indole with Mesityllithium” Chem. Eueopean J. Org, Chem. 2007, 4635-4637.
12. Carolyn S. Reid, Yuhua Zhang and Chao-Jun Li “Fluorous-Tag: An Enabling Isolation Technique for Indium-Mediated Allylation Reactions in Water” Org. Biomole. Chem. 2007, 5, 3589-2591.

Fluorous Scavengers:

1. Emmanuel Baslé, Mickaël Jean, Nicolas Gouault, Jacques Renault and Philippe Uriac “Fluorous scavenger for parallel preparation of tertiary sulfonamides leading to secondary amines” Tetrahedron Lett. 2007, asap.

Fluorous Ligands for Biphasic Catalysis:

1. Liu, Shifang; Xiao, Jianliang “Toward green catalytic synthesis-Transition metal-catalyzed reactions in non-conventional media” Journal of Molecular Catalysis A: Chemical 2007, 270, 1-43.
2. Evgueni Kirillov, Laurent Lavanant, Christophe Thomas, Thierry Roisnel, Yun Chi, Jean-François Carpentier “Chiral Fluorous Dialkoxy-Diamino Zirconium Complexes: Synthesis and Use in Stereospecific Polymerization of 1-Hexene” Chemistry - A European Journal 2007, 13, 923-935.
3. Yi, Wen-Bin; Yin, Ya-Qing; Cai, Chun. “Ytterbium perfluorooctanesulfonate-catalyzed Knoevenagel condensation in a fluorous biphasic system” Organic Preparations and Procedures International  2007, 39, 71-75.
4. Ming-Gui Shen, Chun Cai “Ytterbium perfluorooctanesulfonates catalyzed synthesis of benzimidazole derivatives in fluorous solvents” Journal of Fluorine Chemistry 2007, 128, 232–235.
5. Yan Yin and Gang Zhao “Heptadecafluorooctanesulfonic acid (C8F17SO3H) catalyzed intramolecular hydroamination of olefinic sulfonamides in fluorous biphase system (FBS)” J. Fluorine Chem. 2007, 128, 40-45.
6. Yi, W.-B.; Cai, C. “A novel and highly efficient catalytic system for trinitration of aromatic compounds: ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid in fluorous solvents” Journal of Energetic Materials 2007, 25, 129-139.
7. Shen, Ming-Gui; Cai, Chun. “Rare earth (III) perfluorooctanesulfonates catalyzed synthesis of a-hydroxy-arylacetic acids from aryl methyl ketones in fluorous media” Catalysis Communications 2007, 8, 871-875.
8. Yi WB, Cai C “A Novel And Highly Efficient Catalytic System For Trinitration Of Aromatic Compounds: Ytterbium Perfluorooctanesulfonate And Perfluorooctanesulfonic Acid In Fluorous Solvents” Journal of Energetic Materials 2007, 25, 129-139.
9. Wen-Bin Yi, Chun Cai and Xin Wang “A novel ytterbium/perfluoroalkylated-pyridine catalyst for Baylis–Hillman reaction in a fluorous biphasic system” Journal of Fluorine Chemistry, 2007, 128, 919-924.
10. Wen-Bin Yi, Chun Cai, Xin Wang “A Palladium/Perfluoroalkylated Pyridine Catalyst for Sonogashira Reaction of Aryl Bromides and Chlorides in a Fluorous Biphasic System” European Journal of Organic Chemistry
    2007, 3445-3448.
11. Wen-Bin Yi, Chun Cai and Xin Wang “A novel fluorous palladium catalyst for Heck reaction in a fluorous biphase system (FBS)” Journal of Molecular Catalysis A: Chemical, 2007, 274, 68-71.
12. Norman Lu, Yan-Chou Lin, Jeng-Yung Chen, Chi-Wen Fan and Ling-Kang Liu “New Bis(fluoro-ponytailed) Bipyridine Ligands for Pd-catalyzed Heck Reactions under Fluorous Biphasic Catalysis Condition” Tetrahedron 2007, 63, 2019-2023.
13. Evgueni Kirillov, Laurent Lavanant, Christophe Thomas, Thierry Roisnel, Yun Chi, Jean-François Carpentier “Chiral Fluorous Dialkoxy-Diamino Zirconium Complexes: Synthesis and Use in Stereospecific Polymerization of 1-Hexene” Chemistry - A European Journal 2007, 13, 923-935.
14. 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.
15. Rosenildo Correa da Costa, Frank Hampel, J.A. Gladysz “Crystal structure of an unusual bis(fluorous phosphine)ruthenium(III) complex derived from a fluorous Grubbs’ catalyst” Polyhedron 2007, 26, 581–588.
16. Norman Lu, Yan-Chou Lin, Jeng-Yung Chen, Tsung-Chi Chen, Shih-Chieh Chen, Yuh-Sheng Wen and Ling-Kang Liu “Synthesis, structure and reactivity of novel palladiumdichloride-2,2′-bipyridine with 4,4′-bis(fluorous-ponytail)” Polyhedron 2007, 
17. Funabiki, Kazumasa “Catalytic asymmetric reduction of ketones using fluorous prolinol” Shokubai 2007, 49, 37-41. 
18. Correa da Costa, Rosenildo; Gladysz, John A.   “Syntheses and reactivity of analogues of Grubbs' second generation metathesis catalyst with fluorous phosphines: a new phase-transfer strategy for catalyst activation” Advanced Synthesis & Catalysis 2007, 349, 243-254. 
19. Masaaki Omote, Naoya Tanaka, Atsushi Tarui, Kazuyuki Sato, Itsumaro Kumadaki and Akira Ando “Enantioselective addition of methyl group to aldehydes catalyzed by titanium complex of fluorous ligand” Tetrahedron Letters 2007, 48, 2989-2991.
20. László Mercs, Gianluca Pozzi and Silvio Quici “Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates” Tetrahedron Letters 2007, 3053-3056.
21. Sakiko Goushi, Kazumasa Funabiki, Masaya Ohta, Keisuke Hatano and Masaki Matsui “Novel Fluorous Prolinol as a Pre-catalyst for Catalytic Asymmetric Boran Reduction of Various Ketones” Tetrahedron 2007, 63, 4061–4066.
22. Yasser S. Sokeirik, Hiroyuki Mori, Masaaki Omote, Kazuyuki Sato, Atsushi Tarui, Itsumaro Kumadaki, and Akira Ando “Synthesis of a Fluorous Ligand and Its Application for Asymmetric Addition of Dimethylzinc to Aldehydes” Org. Lett., 2007, 9, 1927-1929.
23. Ma, Yun; Wang, Limin; Shao, Juehua; Tian, He “Recent developments of Lewis acids catalysis: Lanthanide catalysts with long perfluoro-chain in organic chemistry” Current Organic Chemistry 2007, 11, 559-576.
24. Joachim Horn, Willi Bannwarth “Repetitive Application of a Fluorous Chiral BINAP–Ru Complex in the Asymmetric Hydrogenation of Olefins” Eur. J. Org. Chem. 2007, 2058–2063.
25. Cermak J, Zadny J, Krupkova A, et al. “Tetramethyl(perfluoroalkyl)cyclopentadienyl rhodium(III) complexes containing phosphorus and nitrogen monodentate donors. Crystal structure of [(eta(5)-C5Me4C4F9)Rh(PPr3i)Cl-2]” Journal of Organometallic Chemistry 2007, 692, 1557-1570.
26. Omote M, Sato K, Ando A, et al. “Synthesis of axially dissymmetric ligands with two chiral centers of perfluoroalkyl carbinol moiety, and their application to asymmetric syntheses” Current Organic Synthesis 2007, 4, 137-150.
27. Deelman BJ “Fluorous catalysts set to enter the industrial arena” TCE  2007, 24-25.
28. Alan C. Spivey, Christopher J. G. Gripton, Joseph P. Hannah, Chih-Chung Tseng, Paul de Fraine, Nigel J. Parr, Jan J. Scicinski “The development of a ‘safety-catch’ arylgermane for biaryl synthesis by palladium-catalysed germyl-stille cross-coupling” Applied Organometallic Chemistry 2007, 21, 572-589.
29. Crestina S. Consorti, Markus Jurisch, and John A. Gladysz “Ionic Transformations in Extremely Nonpolar Fluorous Media: Phase Transfer Catalysis of Halide Substitution Reactions” Org. Lett. 2007, 9, 2309-2312.
30. Yin Y., Zhao G. “Heptadecafluorooctanesulfonic acid catalyzed intramolecular hydroamination reaction of N-protected” Chemistry Today 2007 (3), 42-45.
31. Seiji Shirakawa, Mitsuhiro Ueda, Youhei Tanaka, Takuya Hashimoto, and Keiji Maruoka “Design of Binaphthyl-Modified Symmetrical Chiral Phase-Transfer Catalysts: Substituent Effect of 4,4’,6,6’-Positions of Binaphthyl Rings in the Asymmetric Alkylation of a Glycine Derivative” Chem. Asian J. 2007, 2, 1276 – 1281.
32. Ming-Gui Shen, Chun Cai, Wen-Bin Yi “A novel fluorous palladium catalyst for Suzuki reaction in fluorous media” J. Fluorine Chem. 2007, asap.
33. Xiuhua Hao, Akihiro Yoshida, Nobuto Hoshi “Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel–Crafts acylation and Prins reaction in fluorous biphase system” J. Fluorine Chem. 2007, asap.
34. Rosenildo Correa da Costa, Frank Hampel, J.A. Gladysz “Crystal structure of an unusual bis(fluorous phosphine) ruthenium(III) complex derived from a Fluorous Grubbs’ catalyst” Polyhedron 2007, 26, 581–588.

Fluorous Biocatalysis:

1. Andrei V. Malkov, Marek Figlus, Sigitas Stonc¡ius, and Pavel Koc¡ovsky “Organocatalysis with a Fluorous Tag: Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by Amino Acid-Derived Formamides” J. Org. Chem. 2007, 72, 1315-1325.
2. Sakiko Goushi, Kazumasa Funabiki, Masaya Ohta, Keisuke Hatano and Masaki Matsui “Novel Fluorous Prolinol as a Pre-catalyst for Catalytic Asymmetric Boran Reduction of Various Ketones” Tetrahedron 2007, 63, 4061–4066.

Fluorous Mixture Synthesis (FMS):

1. David Crich, Daniel Grant, and Albert A. Bowers “Heterobivalent Library Expansion by “Living Radical” Processes: Thiocarbonyl Addition/Elimination, and Nitroxide-Based Reactions with Fluorous Deconvolution” J. Am. Chem. Soc. 2007, 129, asap.
2. Tonoi, Takayuki; Mikami, Koich “Fluorous "racemic" mixture synthesis: simultaneous strategy for demixing and enantioseparation of racemic fluorous-tagged products” European Journal of Organic Chemistry 2007, 11, 1730-1733.