Site-Selective Alkenylation of Unactivated C(sp3)−H Bonds Mediated by Compact Sulfate Radical

Mitsuhiro Ueda, Kazuya Kamikawa, Takahide Fukuyama, Yi Ting Wang, Yen-Ku Wu, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    3 Scopus citations

    Abstract

    A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site-selective alkenylation of unactivated C(sp3)−H bonds with 1,2-bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes (E)-2-alkylvinylphenylsulfones in up to 88 % yield. In contrast with the previously reported decatungstate protocol, the current method is applicable to alkenylation of sterically hindered C−H bonds. This important advantage significantly broadens the substrate scope, and is attributed to the compact size of the sulfate radical employed in the C−H activation and cleavage.

    Original languageEnglish
    Pages (from-to)3545-3550
    Number of pages6
    JournalAngewandte Chemie - International Edition
    Volume60
    Issue number7
    DOIs
    StatePublished - 15 Feb 2021

    Keywords

    • C−H activation
    • radicals
    • sterics
    • synthetic methods
    • tungsten

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