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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1649-1653

http://dx.doi.org/10.1351/pac200072091649

Fluorous methods for synthesis and separation of organic molecules

Dennis P. Curran

Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA

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  • Rustagi Vineeta, Tiwari Rakesh, Verma Akhilesh Kumar: AgI-Catalyzed Cascade Strategy: Regioselective Access to Diversely Substituted Fused Benzimidazo[2,1-a]isoquinolines, Naphthyridines, Thienopyridines, and Quinoxalines in Water. Eur. J. Org. Chem. 2012, 2012, 4590. <http://dx.doi.org/10.1002/ejoc.201200546>
  • Khatun Nilufa, Jamir Latonglila, Ganesh Majji, Patel Bhisma K.: A one-pot strategy for the synthesis of 2-aminobenzothiazole in water by copper catalysis. RSC Adv. 2012, 2, 11557. <http://dx.doi.org/10.1039/c2ra21826g>
  • Li Yu-Nong, Wang Jing-Lun, He Liang-Nian: Copper(II) chloride-catalyzed Glaser oxidative coupling reaction in polyethylene glycol. Tetrahetron Lett 2011, 52, 3485. <http://dx.doi.org/10.1016/j.tetlet.2011.04.118>
  • Saladino Raffaele, Ginnasi Maria Cristina, Collalto Daniela, Bernini Roberta, Crestini Claudia: An Efficient and Selective Epoxidation of Olefins with Novel Methyltrioxorhenium/(Fluorous Ponytailed) 2,2′-Bipyridine Catalysts. Adv Synth Catal 2010, 352, 1284. <http://dx.doi.org/10.1002/adsc.201000032>
  • Curran Dennis P.: ChemInform Abstract: Fluorous Methods for Synthesis and Separation of Organic Molecules. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200126273>
  • Dohi Toshifumi, Yamaoka Nobutaka, Kita Yasuyuki: Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts. Tetrahedron 2010, 66, 5775. <http://dx.doi.org/10.1016/j.tet.2010.04.116>
  • Ding Qiuping, Cao Banpeng, Liu Xianjin, Zong Zhenzhen, Peng Yi-Yuan: Synthesis of 2-aminobenzothiazole via FeCl3-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water. Green Chem 2010, 12, 1607. <http://dx.doi.org/10.1039/c0gc00123f>
  • Wang Jing-Lun, He Liang-Nian, Dou Xiao-Yong, Wu Fang: Poly(ethylene glycol): an Alternative Solvent for the Synthesis of Cyclic Carbonate from Vicinal Halohydrin and Carbon Dioxide. Aust J Chem 2009, 62, 917. <http://dx.doi.org/10.1071/CH08554>
  • Park Gisun, Ko Kwang-Seuk, Zakharova Aleksandra, Pohl Nicola L.: Mono- vs. di-fluorous-tagged glucosamines for iterative oligosaccharide synthesis. J FLUORINE CHEM 2008, 129, 978. <http://dx.doi.org/10.1016/j.jfluchem.2008.05.001>
  • Zhang Liang, Luo Yong, Fan Renhua, Wu Jie: Metal- and solvent-free conditions for the acylation reaction catalyzed by carbon tetrabromide (CBr4). Green Chem 2007, 9, 1022. <http://dx.doi.org/10.1039/b702646c>
  • Mizuno Mamoru, Goto Kohtaro, Miura Tsuyoshi, Inazu Toshiyuki: Rapid Oligosaccharide and Peptide Syntheses on a Recyclable Fluorous Support. QSAR Comb Sci 2006, 25, 742. <http://dx.doi.org/10.1002/qsar.200640043>
  • Mamidyala Sreeman K., Ko Kwang-Seuk, Jaipuri Firoz A., Park Gisun, Pohl Nicola L.: Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays. J FLUORINE CHEM 2006, 127, 571. <http://dx.doi.org/10.1016/j.jfluchem.2006.01.001>
  • Manzoni Leonardo, Castelli Riccardo: Froc:  A New Fluorous Protective Group for Peptide and Oligosaccharide Synthesis. Org Lett 2006, 8, 955. <http://dx.doi.org/10.1021/ol060006e>
  • Wu Jie, Sun Wei, Sun Xiaoyu, Xia Hong-Guang: Expeditious approach to α-amino phosphonates via three-component solvent-free reactions catalyzed by NBS or CBr4. Green Chem 2006, 8, 365. <http://dx.doi.org/10.1039/b517488k>
  • Ikeda Kiyoshi, Mori Hitomi, Sato Masayuki: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor. Chem Commun 2006, 3093. <http://dx.doi.org/10.1039/b605519b>
  • Lai Jacob S., Kool Eric T.: Fluorous Base-Pairing Effects in a DNA Polymerase Active Site. Chem Eur J 2005, 11, 2966. <http://dx.doi.org/10.1002/chem.200401151>
  • Wang Chun-Yan, Meng Wei-Dong, Huang Yan-Gen, Qing Feng-Ling: The synthesis and application of fluorous boronates without perfluorinated solvents. J FLUORINE CHEM 2005, 126, 996. <http://dx.doi.org/10.1016/j.jfluchem.2004.12.014>
  • Miura Tsuyoshi, Tsujino Satoshi, Satoh Ai, Goto Kohtaro, Mizuno Mamoru, Noguchi Midori, Kajimoto Tetsuya, Node Manabu, Murakami Yasuoki, Imai Nobuyuki, Inazu Toshiyuki: Fluorescence modification of Gb3 oligosaccharide and rapid synthesis of oligosaccharide moieties using fluorous protective group. Tetrahedron 2005, 61, 6518. <http://dx.doi.org/10.1016/j.tet.2005.05.001>
  • Miura Tsuyoshi, Satoh Ai, Goto Kohtaro, Murakami Yasuoki, Imai Nobuyuki, Inazu Toshiyuki: A novel benzoyl-type fluorous protecting group for use in fluorous synthesis. Tet Asymm 2005, 16, 3. <http://dx.doi.org/10.1016/j.tetasy.2004.11.050>
  • Goto Kohtaro, Miura Tsuyoshi, Hosaka Daisuke, Matsumoto Hiroharu, Mizuno Mamoru, Ishida Hide-ki, Inazu Toshiyuki: Rapid oligosaccharide synthesis on a fluorous support. Tetrahedron 2004, 60, 8845. <http://dx.doi.org/10.1016/j.tet.2004.07.027>
  • Mizuno Mamoru, Goto Kohtaro, Miura Tsuyoshi, Matsuura Takeshi, Inazu Toshiyuki: Peptide synthesis on fluorous support. Tetrahetron Lett 2004, 45, 3425. <http://dx.doi.org/10.1016/j.tetlet.2004.03.013>
  • Manzoni Leonardo, Castelli Riccardo: Synthesis of the Lewis a Trisaccharide Based on an Anomeric Silyl Fluorous Tag. Org Lett 2004, 6, 4195. <http://dx.doi.org/10.1021/ol048474g>
  • Huang Yangen, Chen Dajun, Qing Feng-Ling: Preparation, properties and synthetic potentials of fluorous boronates. Tetrahedron 2003, 59, 7879. <http://dx.doi.org/10.1016/j.tet.2003.08.034>
  • Sandford Graham: Perfluoroalkanes. Tetrahedron 2003, 59, 437. <http://dx.doi.org/10.1016/S0040-4020(02)01568-5>
  • Zhang Wei: Fluorous technologies for solution-phase high-throughput organic synthesis. Tetrahedron 2003, 59, 4475. <http://dx.doi.org/10.1016/S0040-4020(03)00592-1>
  • Miura Tsuyoshi, Inazu Toshiyuki: Rapid synthesis of oligosaccharide moieties of globotriaosylceramide using fluorous protective group. Tetrahetron Lett 2003, 44, 1819. <http://dx.doi.org/10.1016/S0040-4039(03)00091-1>
  • Dandapani Sivaraman, Curran Dennis P.: Fluorous Mitsunobu reagents and reactions. Tetrahedron 2002, 58, 3855. <http://dx.doi.org/10.1016/S0040-4020(02)00205-3>
  • Liantonio Rosalba, Luzzati Silvia, Metrangolo Pierangelo, Pilati Tullio, Resnati Giuseppe: Perfluorocarbon–hydrocarbon self-assembly. Part 16: Anilines as new electron donor modules for halogen bonded infinite chain formation. Tetrahedron 2002, 58, 4023. <http://dx.doi.org/10.1016/S0040-4020(02)00264-8>
  • Braslau Rebecca, Anderson Marc O, Rivera Frank, Jimenez Armando, Haddad Terra, Axon Jonathan R: Acyl hydrazines as precursors to acyl radicals. Tetrahedron 2002, 58, 5513. <http://dx.doi.org/10.1016/S0040-4020(02)00490-8>