A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol

Tae Bo Sim, Jaesung Choi, Meyoung Ju Joung, Nung Min Yoon

    Research output: Contribution to journalArticlepeer-review

    36 Citations (Scopus)

    Abstract

    The radical addition reaction of alkyl iodides with α,β-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50-95%) using Ni(OAc)2 (0.05-0.2 equiv) - BER (3-5 equiv) in methanol in 1-9 h at room temperature or at 65°C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride - BER can be removed readily by filtration.

    Original languageEnglish
    Pages (from-to)2357-2361
    Number of pages5
    JournalJournal of Organic Chemistry
    Volume62
    Issue number8
    DOIs
    Publication statusPublished - 1997

    ASJC Scopus subject areas

    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol'. Together they form a unique fingerprint.

    Cite this