Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation

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

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    2 Scopus citations

    Abstract

    A radical chain addition of allyl bromides 2 to alkenylcyclopropanes 1 resulted in [3+2] annulation to give 2-bromomethyl-alkenylcyclopentanes 3 in good yields (16 examples). In this reaction, two kinetically fast radical reactions, cyclopropylcarbinyl radical-ring-opening and 5-exo-radical cyclization, preceded the β-fragmentation of a bromine radical to make the formal cycloaddition possible.

    Original languageEnglish
    Pages (from-to)1525-1528
    Number of pages4
    JournalScience China Chemistry
    Volume62
    Issue number11
    DOIs
    StatePublished - Nov 2019

    Keywords

    • alkenylcyclopentanes
    • alkenylcyclopropanes
    • bromine radical
    • photo irradiation
    • [3+2] annulation

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