Synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers by the reaction of dithiocarbonates with IF5-pyridine-HF
作者： Toshiya Inoue , Chiaki Fuse , Shoji Hara
DOI: 10.1016/J.JFLUCHEM.2015.04.016
关键词:
摘要: Abstract Trifluoromethyl ether and difluoro(methylthio)methyl of phenols aliphatic alcohols were selectively synthesized from the corresponding dithiocarbonates. When IF 5 -pyridine-HF was used alone in reaction dithiocarbonate, formed. On other hand, by additional use Et 3 N-6HF with -pyridine-HF, trifluoromethyl formed selectively. Various functional groups such as ester, ether, amide, acetonide could tolerate conditions, various functionalized ethers synthesized.
elsevier.com
sci-hub.se 参考文章(24)
Kiyoshi Kanie, Yoichiro Tanaka, Kazundo Suzuki, Manabu Kuroboshi, Tamejiro Hiyama, A Convenient Synthesis of Trifluoromethyl Ethers by Oxidative Desulfurization-Fluorination of Dithiocarbonates Bulletin of the Chemical Society of Japan. ,vol. 73, pp. 471- 484 ,(2000) , 10.1246/BCSJ.73.471
Frédéric Leroux, Peter Jeschke, Manfred Schlosser, α-Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species Chemical Reviews. ,vol. 105, pp. 827- 856 ,(2005) , 10.1021/CR040075B
Guosheng Liu, Pinhong Chen, Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations Synthesis. ,vol. 45, pp. 2919- 2939 ,(2013) , 10.1055/S-0033-1339677
Kiyoshi Kanie, Yoichiro Tanaka, Masaki Shimizu, Manabu Kuroboshi, Tamejiro Hiyama, OXIDATIVE DESULFURIZATION-FLUORINATION OF ALKANOL XANTHATES. CONTROL OF THE REACTION PATHWAY TO FLUORINATION OR TRIFLUOROMETHOXYLATION Chemical Communications. pp. 309- 310 ,(1997) , 10.1039/A607897D
Yvan Carcenac, Marc Tordeux, Claude Wakselman, Patrick Diter, Experimental determination of the conformational free energies (A values) of fluorinated substituents in cyclohexane by dynamic 19F NMR spectroscopy. Part 2. Extension to fluoromethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio and trifluoromethoxy groups New Journal of Chemistry. ,vol. 30, pp. 447- 457 ,(2006) , 10.1039/B516641A
Masataka Kunigami, Shoji Hara, Synthesis of fluoromethyl ethers and fluoromethyl esters by the reaction of the corresponding methylthiomethyl ethers and methylthiomethyl esters with IF5-pyridine-HF Journal of Fluorine Chemistry. ,vol. 167, pp. 101- 104 ,(2014) , 10.1016/J.JFLUCHEM.2014.05.008
George L. Trainor, The Preparation of O-Trifluoromethyl Carbohydrates Journal of Carbohydrate Chemistry. ,vol. 4, pp. 545- 563 ,(1985) , 10.1080/07328308508082676
Manabu Kuroboshi, Kiyoshi Kanie, Tamejiro Hiyama, Oxidative desulfurization-fluorination: A facile entry to a wide variety of organofluorine compounds leading to novel liquid-crystalline materials Advanced Synthesis & Catalysis. ,vol. 343, pp. 235- 250 ,(2001) , 10.1002/1615-4169(20010330)343:3<235::AID-ADSC235>3.0.CO;2-0
Iris Ben-David, Dalit Rechavi, Eyal Mishani, Shlomo Rozen, A novel synthesis of trifluoromethyl ethers via xanthates, utilizing BrF3 Journal of Fluorine Chemistry. ,vol. 97, pp. 75- 78 ,(1999) , 10.1016/S0022-1139(99)00031-7
Teruo Umemoto, Electrophilic Perfluoroalkylating Agents. Chemical Reviews. ,vol. 96, pp. 1757- 1778 ,(1996) , 10.1021/CR941149U