[3,3]-Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides with Alkyl Nitriles

摘要

Herein we report the ortho-cyanoalkylation of aryl fluoroalkyl sulfoxides with alkyl nitriles. The reaction proceeds through an "assembly/deprotonation" triggered [3,3]-rearrangement and allows the incorporation of two valuable functional groups including the cyano group and difluoromethylthio group into arenes. As a consequence, a wide range of ortho-cyanoalkylated difluoromethylthio arenes were produced with high efficiency under mild and environmentally friendly conditions. Remarkably, the reaction proceeds smoothly with the electron-donating group substituted arenes which can be challenging to the reaction of non-fluoroalkyl sulfoxides. This beneficial effect can be attributed to the unique electronegativity of fluoroalkyl substituents.