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Copper-Catalyzed Direct Alkylation of Perfluoroarenes with Hydrocarbons

preprint
submitted on 24.12.2019 and posted on 26.12.2019 by Weilong Xie, Joon Heo, Dongwook Kim, Sukbok Chang
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 )‒C(sp3 ) 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 C‒H bonds.

History

Email Address of Submitting Author

sbchang@kaist.ac.kr

Institution

KAIST and IBS

Country

South Korea

ORCID For Submitting Author

0000-0001-9069-0946

Declaration of Conflict of Interest

No

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