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Metal-Free Direct 1,6- and 1,2-Difunctionalization Triggered by Radical Trifluoromethylation of Alkenes
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    Metal-Free Direct 1,6- and 1,2-Difunctionalization Triggered by Radical Trifluoromethylation of Alkenes
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    Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, P. R. China
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    Organic Letters

    Cite this: Org. Lett. 2015, 17, 6, 1589–1592
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    https://doi.org/10.1021/acs.orglett.5b00479
    Published March 12, 2015
    Copyright © 2015 American Chemical Society

    Abstract

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    A metal-free direct remote C–H functionalization triggered by radical trifluoromethylation of alkenes was explored, realizing highly selective 1,6-difunctionalization of alkenes toward valuable trifluoromethyl α-hydroxycarbonyl compounds. Furthermore, a metal-free direct intermolecular regioselective 1,2-oxytrifluoromethylation of alkenes is also disclosed. With Togni’s reagent as both the CF3 source and oxidant, the reaction exhibits a broad substrate scope with excellent functionality tolerance under mild metal-free conditions, thus showing great potential for synthetic utility.

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    Experimental procedures, characterization of all new compounds, Table S1, Figure S1, Scheme S1, and X-ray data (CIF) of 4pa. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2015, 17, 6, 1589–1592
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.5b00479
    Published March 12, 2015
    Copyright © 2015 American Chemical Society

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