Cationic lr(l)-catalyzed sp3 C- H bond alkenylation of amides with alkynes

Kyoji Tsuchikama, Mitsugu Kasagawa, Kohei Endo, Takanori Shibata

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    Abstract

    A cationic lr(l)-BINAP catalyst cleaved sp3 C-H bonds of arylamides rather than sp2 C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.

    Original languageEnglish
    Pages (from-to)1821-1823
    Number of pages3
    JournalOrganic Letters
    Volume11
    Issue number8
    DOIs
    Publication statusPublished - 2009 Apr 16

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    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

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