Coupling routes to hexafluoro-1,3-butadiene, substituted-1,3-fluorine-containing butadienes and fluorinated polyenes
作者:Donald J. Burton、Steven W. Hansen、Peter A. Morken、Kathryn J. MacNeil、Charles R. Davis、Ling Xue
DOI:10.1016/j.jfluchem.2007.11.004
日期:2008.5
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 CuBr(2) 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 CuBr(2) or FeCl(3). 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 alpha,beta-difluoro-beta-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. (c) 2007 Elsevier B.V. All rights reserved.