Cationic iridium-catalyzed synthesis initiated by the cleavage of C-H, N-H, and C-O bonds

Takanori Shibata, Kyoji Tsuchikama, Shiguang Pan

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    The direct functionalization of inactive bonds is an ideal transformation in organic synthesis because the introduction of activating groups, such as halogens and metals, to substrates is unnecessary and by-products derived from them are not formed. This report describes several types of cationic iridium-catalyzed reactions that occur through C-H, N-H, or C-O bond cleavage. The carbonyl-directed sp2 C-H bond activation of aryl ketones realized new approaches to benzofulvene, benzofuran and indole synthesis, as well as the C2-position-selective alkylation of N-acyl-protected indoles. The enantioselective sp3 C-H alkylation of 2-(alkylamino)pyridines and the intermolecular enantioselective hydroamination of heteroaromatic amines gave various chiral amines. 0-to-7V-alkyl migration in 2-alkoxypyridines gave 7V-alkylpyridones via C-O bond cleavage.

    Original languageEnglish
    Pages (from-to)1182-1194
    Number of pages13
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume71
    Issue number11
    DOIs
    Publication statusPublished - 2013

    Fingerprint

    Iridium
    Alkylation
    Amines
    Pyridines
    Indoles
    Halogens
    Ketones
    Byproducts
    Metals
    Chemical activation
    Substrates
    indole
    benzofuran

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Cationic iridium-catalyzed synthesis initiated by the cleavage of C-H, N-H, and C-O bonds. / Shibata, Takanori; Tsuchikama, Kyoji; Pan, Shiguang.

    In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 71, No. 11, 2013, p. 1182-1194.

    Research output: Contribution to journalArticle

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