Fluorous chemistry has been growing rapidly for two decades. While many perfluoroalkyl-tagged molecules have been prepared for fluorous studies, the coupling methodologies used to append perfluoroalkyl ponytails to aromatic molecules are limited. Also, it has been observed that the spacers between perfluoroalkyl ponytails and functional groups, which are often an artifact of the coupling methodology, can affect the solubility and electronic properties of the molecules. Therefore, new methods to prepare fluorous molecules with different spacers are needed. Herein we report a new method to access perfluoroalkyl aromatic molecules with the -CH2CH2- spacer via the Heck reaction. A variety of aryl substrates, such as heteroarenes, multi-functionalized arenes, and electron-rich arenes, were successfully coupled with perfluoroalkyl ponytails in moderate to excellent yields

Preparing perfluoroalkyl substituted arenes via the Heck reaction

248th National Meeting (2014)

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