Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format

Frady G. Adly, Ashraf Ghanem

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).
    Original languageEnglish
    Pages (from-to)852-857
    Number of pages6
    JournalTetrahedron Letters
    Volume57
    Issue number8
    DOIs
    Publication statusPublished - 24 Feb 2016

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    Miniaturization
    Catalyst supports
    Leaching
    Polymers
    Catalysts
    pyridine
    cyclopropane

    Cite this

    @article{db25454ea59f4d5389742a5ce5cf941f,
    title = "Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format",
    abstract = "Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44{\%}) and excellent diastereoselectivity (>20:1 E:Z dr).",
    keywords = "Cyclopropanation, Dirhodium, Metal-carbenoids, Microreactor, Rh2(S-PTTL)4, Rh2(S-tertPTTL)4, Rh-2(S-PTTL)(4), Rh-2(S-(PTTL)-P-tert)(4)",
    author = "Adly, {Frady G.} and Ashraf Ghanem",
    year = "2016",
    month = "2",
    day = "24",
    doi = "10.1016/j.tetlet.2016.01.010",
    language = "English",
    volume = "57",
    pages = "852--857",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "8",

    }

    Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format. / Adly, Frady G.; Ghanem, Ashraf.

    In: Tetrahedron Letters, Vol. 57, No. 8, 24.02.2016, p. 852-857.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Polymer monolith-supported dirhodium(II)-catalyzed continuous flow cyclopropanation in capillary format

    AU - Adly, Frady G.

    AU - Ghanem, Ashraf

    PY - 2016/2/24

    Y1 - 2016/2/24

    N2 - Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).

    AB - Herein, the first trial for the miniaturization of the dirhodium(II)-catalyzed cyclopropanation reaction is reported. Rh2(S-tertPTTL)4†was immobilized inside a capillary microreactor on a pyridine-derived monolithic support. The system demonstrated good stability with low leaching rate of the dirhodium(II) catalyst comparable to conventional packed solid support. The Rh2(S-tertPTTL)4-catalyzed cyclopropanation microreaction was carried out under continuous flow conditions generating the cyclopropane product in moderate yield (44%) and excellent diastereoselectivity (>20:1 E:Z dr).

    KW - Cyclopropanation

    KW - Dirhodium

    KW - Metal-carbenoids

    KW - Microreactor

    KW - Rh2(S-PTTL)4

    KW - Rh2(S-tertPTTL)4

    KW - Rh-2(S-PTTL)(4)

    KW - Rh-2(S-(PTTL)-P-tert)(4)

    UR - http://www.mendeley.com/research/polymer-monolithsupported-dirhodiumiicatalyzed-continuous-flow-cyclopropanation-capillary-format

    U2 - 10.1016/j.tetlet.2016.01.010

    DO - 10.1016/j.tetlet.2016.01.010

    M3 - Article

    VL - 57

    SP - 852

    EP - 857

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 8

    ER -