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Text-submitted-S. Chang.pdf (1.69 MB)

Copper-Catalyzed Direct Alkylation of Perfluoroarenes with Hydrocarbons

preprint
submitted on 24.12.2019, 07:55 and posted on 26.12.2019, 05:05 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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