Preparation of (E)-1-aryl-3,3,3-trifluoro-1,2-di(trimethylsilyl)-1-propenes via stereoselective bissilylation of trifluoromethyl aryl acetylenes and electrophilic substitution of its TMS groups |
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Authors: | Toshimasa Katagiri Hayato NakanishiKenichi Ohno Takayuki SeikiAkira Isobe Keisuke KataokaKenji Uneyama |
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Institution: | Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushimanaka 3-1-1, Kita-ku, Okayama 700-8530, Japan |
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Abstract: | Preparations and reactions of (E)-1-aryl-3,3,3-trifluoro-1,2-di(trimethylsilyl)-1-propenes are described. (E)-1-Aryl-3,3,3-trifluoro-1,2-di(trimethylsilyl)-1-propene was prepared from aryl trifluoromethyl acetylenes via reductive bissilylation by TMSCl/Mg in good yields. The silyl groups of (E)-3,3,3-trifluoro-1,2-di(trimethylsilyl)-1-phenyl-1-propene were substituted by electrophiles in both a stepwise and stereoselective (and/or stereospecific) manner. This compound could be a building block for preparations of substituted trifluoropropenes. |
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Keywords: | Reductive bissilylation Trifluoromethylated olefin Trifluoropropene Stereoselective anti addition |
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