These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
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.
submitted on 24.12.2019, 07:55 and posted on 26.12.2019, 05:05by 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
) 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