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First practical synthesis of 2- or 3-fluoroalkylated indenols via cobalt-catalyzed [2 + 3] carbocyclization of fluorine-containing alkynes and 2-iodoaryl ketones
Affiliation:1. Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan;2. Department of Quantum Beam Science, Graduate School of Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki, 316-8551, Japan;1. Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan;2. Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo, Sagamihara, Kanagawa 252-5258, Japan;1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation;2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation;1. Department of Chemistry, University of Science and Technology of China, Hefei 230026, China;2. Department of Polymer Science and Engineering, University of Science and Technology Beijing, Beijing 100083, China
Abstract:[2 + 3] Cycloaddition reaction of fluorine-containing alkynes with various 2-iodoaryl ketones in the presence of CoCl2(dppf) catalyst proceeded very smoothly to give the corresponding 2- or 3-fluoroalkylated indenols in 57–98% yields. These regioisomers could be successfully separated and obtained in a pure form. From X-ray crystallographic and NOESY analyses, major or minor regioisomers were determined as 3- or 2-fluoroalkylated indenols, respectively.
Keywords:Fluoroalkylated indenols  Cobalt catalyst  [2 + 3] Carbocyclization  Fluorine-containing alkynes  2-Iodoaryl ketones
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