Site-Selective C(sp3)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst

Takahide Fukuyama, Tomohiro Nishikawa, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Scopus citations

    Abstract

    The TBADT-catalyzed C(sp3)–H functionalization of perfluorophenyl- and perfluoroalkyl-substituted alkanes was studied to determine how the fluorous substituents affect site-selectivity. Alkylation of alkyl-substituted perfluorobenzene avoids α-C–H bonds, unlike their alkylbenzene counterparts, allowing site-selective functionalization of C–H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided α-C–H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of α-C–H functionalization.

    Original languageEnglish
    Pages (from-to)1424-1428
    Number of pages5
    JournalEuropean Journal of Organic Chemistry
    Volume2020
    Issue number10
    DOIs
    StateAccepted/In press - Jan 2019

    Keywords

    • C–H functionalization
    • Photocatalysis
    • Radical reactions
    • Synthetic methods

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