Pd/light-induced alkyl-alkenyl coupling reaction between unactivated alkyl iodides and alkenylboronic acids

Hsin Ju Huang, Yi Ting Wang, Yen-Ku Wu, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Alkyl-alkenyl coupling reaction between unactivated alkyl iodides and 2-arylalkenylboronic acids utilizing a Pd/light combined system was studied. This reaction provided 2-alkylarylalkenes in good yields. It is proposed that in this reaction alkyl radicals are formed by SET from a Pd catalyst to alkyl iodides, which then undergo addition reactions to form C-C double bonds of alkenyl boronic acids and the subsequent β-fragmentation of boronyl radicals leads to the formation of alkyl-substituted arylalkenes.

    Original languageEnglish
    Pages (from-to)1266-1270
    Number of pages5
    JournalOrganic Chemistry Frontiers
    Volume7
    Issue number10
    DOIs
    StatePublished - 21 May 2020

    Keywords

    • SUZUKI CROSS-COUPLINGS
    • RATE CONSTANTS
    • HECK REACTION
    • BORONIC ACIDS
    • SECONDARY
    • HALIDES
    • CYCLOPROPYLCARBINYL
    • BROMIDES
    • ESTER
    • CHLORIDES

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