Bromine-Radical-Mediated Site-Selective Allylation of C(sp 3 )-H Bonds

Mitsuhiro Ueda, Ayami Maeda, Kanako Hamaoka, Mika Sasano, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    5 Scopus citations

    Abstract

    The C(sp 3 )-H allylation of alkanes is investigated by using allyl bromides under radical reaction conditions. In many cases, methine C-H allylation preceded methylene and methyl C-H allylation with complete or a high degree of site selectivity. The C-H allylation of allylic compounds, such as allylbenzene, gives 1,5-dienes with the S H 2′ reactions of the allyl radicals occurring at the less hindered carbon.

    Original languageEnglish
    Pages (from-to)1171-1177
    Number of pages7
    JournalSynthesis (Germany)
    Volume51
    Issue number5
    DOIs
    StatePublished - Jan 2019

    Keywords

    • C(sp3)–H allylation
    • SH2 reaction
    • SH2′ reaction
    • bromine radicals
    • site selectivity

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