On treating 1,3,4-tribromo-1,1,2,2-tetrafluorobutane, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, with 3.3 equivalents of LHMDS at 0 °C in THF, the corresponding lithium acetylide could be prepared quantitatively. The acetylide reacted well with various aldehydes, ketones, or chlorosilanes to give the corresponding acetylene derivatives in high yields. It was also found that various iodoarenes could participate in the cross-coupling reaction with the zinc acetylide, readily prepared from the lithium acetylide and ZnCl₂·TMEDA complex, in the presence of Pd(PPh₃)₄ to bring about the adducts in high yields. Thus-obtained acetylene derivatives underwent smooth Diels–Alder reaction with various 1,3-dienes to afford the corresponding 1,4- or 1,3-cyclohexadiene derivatives. In addition, it was revealed that the oxidative aromatization of the resulting cyclohexadiene derivatives with DDQ took place very smoothly, providing the multi-substituted benzene derivatives having a tetrafluoro­ethylene group.

中文翻译：

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含四氟乙烯（CF2CF2）的乙炔衍生物的合成及应用

在处理1,3,4-三溴-1,1,2,2-四氟丁烷时，很容易从市售的4-溴-3,3,4,4-四氟丁-1-烯制得，当量为3.3的LHMDS在THF中，在室温下，可以定量制备相应的乙炔化锂。乙炔与各种醛，酮或氯硅烷反应良好，以高收率得到相应的乙炔衍生物。还发现，在Pd（PPh ₃）₄存在下，各种碘代芳烃都可以参与由乙炔酸锂和ZnCl ₂ ·TMEDA络合物容易制备的与乙炔锌的交叉偶联反应。以高收率生产加合物。如此获得的乙炔衍生物与各种1,3-二烯进行平滑的Diels-Alder反应，得​​到相应的1,4-或1,3-环己二烯衍生物。另外，发现得到的环己二烯衍生物用DDQ的氧化芳构化非常顺利，提供了具有四氟乙烯基的多取代苯衍生物。