Bromine-Radical-Mediated Synthesis of β-Functionalized β,γ- and δ,ϵ-Unsaturated Ketones via C-H Functionalization of Aldehydes

Takashi Kippo, Yuki Kimura, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Scopus citations

    Abstract

    The bromine-radical-mediated allylation reaction of aldehydes was studied. In the presence of V-65 as radical initiator, the reaction of aldehydes with allyl bromides gave β,γ-unsaturated ketones in good yields (13 examples, 45-84%). The reaction is triggered by hydrogen abstraction from the aldehyde by bromine radical to form an acyl radical, which undergoes an S H 2′-type addition-elimination reaction with allyl bromides to give coupling products with liberation of bromine radical. Three-component coupling reactions comprising aldehydes, electron-deficient alkenes, and methallyl bromide also proceeded to give δ,ϵ-unsaturated ketones.

    Original languageEnglish
    Pages (from-to)1733-1737
    Number of pages5
    JournalSynlett
    Volume28
    Issue number14
    DOIs
    StatePublished - 1 Sep 2017

    Keywords

    • SH2′ reaction
    • bromine radical
    • three-component reaction
    • β,γ-unsaturated ketones
    • δ,ϵ-unsaturated ketones

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