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Text-submitted-S. Chang.pdf (1.69 MB)
Copper-Catalyzed Direct Alkylation of Perfluoroarenes with Hydrocarbons
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
Construction of carbon–carbon bonds is one of the most essential tools in chemical synthesis. In the previously
established cross-coupling reactions, pre-functionalized starting materials are employed usually in the form of arylor alkyl (pseudo)halides or their metallated derivatives. However, direct use of arenes and alkanes via a twofold
oxidative C–H bond activation strategy to access chemoselective C(sp2
) cross-couplings is highly
challenging due to the low reactivity of carbon–hydrogen (C–H) bonds and the difficulty in suppressing side
reactions such as homocouplings. Herein, we present a copper-catalyzed cross-dehydrogenative coupling of perfluoroarenes with alkanes. Mechanistic information was obtained by combining experimental and computational
studies to suggest that the optimal diketimine copper catalyst system plays a dual role to activate both sp3 and sp2