Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles

Takanori Shibata, Hiroyuki Hirashima, Mitsugu Kasagawa, Kyoji Tsuchikama, Kohei Endo

    Research output: Contribution to journalArticle

    24 Citations (Scopus)

    Abstract

    Secondary sp3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.

    Original languageEnglish
    Article numberU05011ST
    Pages (from-to)2171-2176
    Number of pages6
    JournalSynlett
    Issue number15
    DOIs
    Publication statusPublished - 2011

    Fingerprint

    Alkenylation
    Indoles
    Alkynes
    Urea
    Isomerization
    Nitrogen
    Chemical activation
    Atoms
    Catalysts

    Keywords

    • C-H bond activation
    • directing group
    • indoles
    • iridium
    • ureas

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles. / Shibata, Takanori; Hirashima, Hiroyuki; Kasagawa, Mitsugu; Tsuchikama, Kyoji; Endo, Kohei.

    In: Synlett, No. 15, U05011ST, 2011, p. 2171-2176.

    Research output: Contribution to journalArticle

    Shibata, Takanori ; Hirashima, Hiroyuki ; Kasagawa, Mitsugu ; Tsuchikama, Kyoji ; Endo, Kohei. / Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles. In: Synlett. 2011 ; No. 15. pp. 2171-2176.
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