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Hydroarylation of Alkenes by protonation/Friedel-Crafts Trapping – HFIP-Mediated Access to Per-Aryl Quaternary Stereocentres

preprint
submitted on 29.04.2019, 11:42 and posted on 30.04.2019, 17:12 by Christian Nielsen, Andrew J. P. White, David Sale, Jordi Bures, Alan Spivey

Upon treatment with a combination of HFIP and a strong Brønsted acid, alkenes behave as Brønsted bases and protonate to give carbocations which can be trapped by electron rich arenes. The reaction constitutes a Friedel-Crafts (FC) hydroarylation which proceeds with Markovnikov selectivity and is orthogonal to traditional metal catalyzed processes. The products contain polyarylated quaternary carbon atoms which are difficult to obtain via alternative methods. Intermolecular transfer hydrogenation and hydrothiolation are also demonstrated.

History

Email Address of Submitting Author

cn1311@ic.ac.uk

Institution

Imperial College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-6731-1888

Declaration of Conflict of Interest

No conflict of interest

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