Coupling routes to hexafluoro-1,3-butadiene, substituted-1,3-fluorine-containing butadienes and fluorinated polyenes

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• 作者：Donald J. Burton ; Steven W. Hansen ; Peter A. Morken ; Kathryn J. MacNeil ; Charles R. Davis ; Ling Xue
• 关键词：Hexafluoro-1 ; 3-butadiene ; Perfluoro-2 ; 3-dimethyl-1 ; 3-butadiene ; (Z)(Z)-1 ; 4-aryl-1 ; 3-tetafluorobutadiene ; (2E)(4E)(6E)(8E)-perfluorodecatetraene ; Trifluorovinylzinc reagent ; Pentafluoropropenyl-2-zinc reagent ; Pent
• 刊名：Journal of Fluorine Chemistry
• 出版年：2008
• 出版时间：May 2008
• 年：2008
• 卷：129
• 期：5
• 页码：435-442
• 全文大小：219 K

文摘

Hexafluoro-1,3-butadiene was readily prepared via a variety of self-coupling processes, such as Cu(0) mediated self-coupling of iodotrifluoroethene, Pd(0) catalyzed coupling of iodotrifluoroethene with the trifluorovinylzinc reagent, and CuBr₂ mediated coupling of the trifluorovinylzinc reagent. Perfluoro-2,3-dimethyl-1,3-butadiene was readily synthesized by the reaction of pentafluoropropenyl-2-zinc reagent with either CuBr₂ or FeCl₃. Alternatively, perfluoro-2,3-dimethyl-1,3-butadiene was prepared by oxidation of the pentafluoropropenyl-2-copper reagent with dioxygen. Cu(0) mediated coupling of an (E)-substituted ,β-difluoro-β-iodostyrene provided the first useful route to a (Z)(Z)-1,4-diaryl-1,3-tetrafluorobutadiene. Extension of the Cu(0) mediated coupling methodology to a perfluorodienyl iodide demonstrated a useful stereospecific route to perfluoropolyenes.