Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Takahide Fukuyama, Takanobu Bando, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    7 Scopus citations

    Abstract

    A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

    Original languageEnglish
    Article numberss-2018-c0146-st
    Pages (from-to)3015-3021
    Number of pages7
    JournalSynthesis (Germany)
    Volume50
    Issue number15
    DOIs
    StatePublished - Aug 2018

    Keywords

    • carbonylation
    • electron transfer
    • lactams
    • lactones
    • metal-free
    • radical reactions

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