C-Si bond formation and fluoro(2.2)cylophane synthesis by C-F bond activation

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Fluorocyclophanes have been recognized as a promising monomer for thermally stable insulator polymer useful for large scale semiconductor manufacturing. In order to develop a practical synthetic method for the cyclophane, Mg-promoted C-F bond activtion has been extensively studied. And one of the protocol for the purpose has been found which consists of reaction of bistrifluoromethyl benzene wirh magnesium in the presence of trimethylsilane in DMF. The reaction provided the desired trimethylsilylated benzyl compound in 50-60% yields. Fluroride-catalyzed desilylated defluorination gave the desired cyclophane via quinodimethane in 53% yield. The present method will be competitive to the Dolbier method based on Zn-metal promoted dechlorinative preparation from the point of availability of bistrifluoromethylbenzene.