Bromoallylation of alkenes leading to 4-alkenyl bromides based on trapping of β-bromoalkyl radicals

Takashi Kippo, Kanako Hamaoka, Mitsuhiro Ueda, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    3 Scopus citations

    Abstract

    A radical-chain addition of allyl bromides to aryl alkenes, vinyl ester, and vinyl phthalimide was studied in which elusive β-bromoalkyl radicals were trapped efficiently to give 5-bromo-1-pentenes in good to high yields (16 examples). A subsequent carbonylative radical cyclization with AIBN/Bu3SnH/CO was successful in giving the corresponding 3,5-disubstituted cyclohexanone derivatives in moderate yields. Synthesis of a piperidine ring was also successful by subsequent reaction with primary amine.

    Original languageEnglish
    Pages (from-to)5198-5200
    Number of pages3
    JournalOrganic Letters
    Volume19
    Issue number19
    DOIs
    StatePublished - 6 Oct 2017

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