For the development of OLEDs and ionic liquids, and in crystal engineering polyfluorinated compounds have been used in many studies. However, the synthesis of these compounds can be challenging due to the electron-deficiency of these compounds. Especially cross-coupling reactions have limitations in that respect.<br/>Herein we present our results concerning the synthesis of polyfluorinated bi-, ter- and quaterphenyl derivatives via Suzuki-coupling reactions. For this purpose, we screened a variety of different Buchwald phosphine ligands for the synthesis of polyfluorinated biphenyls. During this we also looked into the effects of other reaction conditions, such as temperature, solvents, bases and the influence of the boronic acid. Especially the latter, as we found out, plays an important role in the prevention of side reactions such as homocouplings. This must be avoided, since it is near to impossible to separate these product mixtures afterwards. We were able to optimize these reactions towards yields up to 98% with no significant side reactions and therefore simple work ups. Furthermore, we applied these findings to the syntheses of functionalized biphenyls and in addition obtained ter- and quarterphenyls by multiple couplings in one-pot syntheses. Our results should make these types of compounds more readily accessible in the future.

Synthesis of polyfluorinated biphenyls and polyphenyls with Buchwald phosphine ligand assisted Suzuki-Coupling

253rd National Meeting (2017)

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