Upward Trend in Catalytic Efficiency of Rare-Earth Triflate Catalysts in Friedel-Crafts Aromatic Sulfonylation Reactions

Fritz Duus, Thach Ngoc Le, Vo Thu An Nguyen

    Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

    Resumé

    A series of 14 lanthanide (Ln) triflates were investigated as sustainable catalysts for aromatic sulfonylation reactions under microwave irradiation. The catalytic efficiency of the early triflates La(OTf)3–Eu(OTf)3 is good for long irradiation times. For the later lanthanides, yields reaching over 90 % were achieved for short irradiation periods. This was the case especially for Tm(OTf)3, Yb(OTf)3, and Lu(OTf)3, of which Yb(OTf)3 was the most efficient. The upward trend in catalytic efficiency therefore correlates with the lanthanide sequence in the periodic table. The results can be explained by the decrease in the radii of the Ln3+ ions, and the hydrolysis and water-exchanges rate within the series. The results are in agreement with the first principal property value (t1) calculated by principal component analysis (PCA) published previously. A large drop in sulfonylation yield was obtained with Gd(OTf)3, which matched the “gadolinium break”; the well-known discontinuity in lanthanide properties
    OriginalsprogEngelsk
    TidsskriftAsian Journal of Organic Chemistry
    Vol/bind3
    Udgave nummer9
    Sider (fra-til)963-968
    Antal sider6
    ISSN2193-5807
    DOI
    StatusUdgivet - 2014

    Citer dette

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    title = "Upward Trend in Catalytic Efficiency of Rare-Earth Triflate Catalysts in Friedel-Crafts Aromatic Sulfonylation Reactions",
    abstract = "A series of 14 lanthanide (Ln) triflates were investigated as sustainable catalysts for aromatic sulfonylation reactions under microwave irradiation. The catalytic efficiency of the early triflates La(OTf)3–Eu(OTf)3 is good for long irradiation times. For the later lanthanides, yields reaching over 90 {\%} were achieved for short irradiation periods. This was the case especially for Tm(OTf)3, Yb(OTf)3, and Lu(OTf)3, of which Yb(OTf)3 was the most efficient. The upward trend in catalytic efficiency therefore correlates with the lanthanide sequence in the periodic table. The results can be explained by the decrease in the radii of the Ln3+ ions, and the hydrolysis and water-exchanges rate within the series. The results are in agreement with the first principal property value (t1) calculated by principal component analysis (PCA) published previously. A large drop in sulfonylation yield was obtained with Gd(OTf)3, which matched the “gadolinium break”; the well-known discontinuity in lanthanide properties",
    author = "Fritz Duus and Le, {Thach Ngoc} and Nguyen, {Vo Thu An}",
    year = "2014",
    doi = "10.1002/ajoc.201402067",
    language = "English",
    volume = "3",
    pages = "963--968",
    journal = "Asian Journal of Organic Chemistry",
    issn = "2193-5807",
    publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
    number = "9",

    }

    Upward Trend in Catalytic Efficiency of Rare-Earth Triflate Catalysts in Friedel-Crafts Aromatic Sulfonylation Reactions. / Duus, Fritz; Le, Thach Ngoc; Nguyen, Vo Thu An.

    I: Asian Journal of Organic Chemistry, Bind 3, Nr. 9, 2014, s. 963-968.

    Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

    TY - JOUR

    T1 - Upward Trend in Catalytic Efficiency of Rare-Earth Triflate Catalysts in Friedel-Crafts Aromatic Sulfonylation Reactions

    AU - Duus, Fritz

    AU - Le, Thach Ngoc

    AU - Nguyen, Vo Thu An

    PY - 2014

    Y1 - 2014

    N2 - A series of 14 lanthanide (Ln) triflates were investigated as sustainable catalysts for aromatic sulfonylation reactions under microwave irradiation. The catalytic efficiency of the early triflates La(OTf)3–Eu(OTf)3 is good for long irradiation times. For the later lanthanides, yields reaching over 90 % were achieved for short irradiation periods. This was the case especially for Tm(OTf)3, Yb(OTf)3, and Lu(OTf)3, of which Yb(OTf)3 was the most efficient. The upward trend in catalytic efficiency therefore correlates with the lanthanide sequence in the periodic table. The results can be explained by the decrease in the radii of the Ln3+ ions, and the hydrolysis and water-exchanges rate within the series. The results are in agreement with the first principal property value (t1) calculated by principal component analysis (PCA) published previously. A large drop in sulfonylation yield was obtained with Gd(OTf)3, which matched the “gadolinium break”; the well-known discontinuity in lanthanide properties

    AB - A series of 14 lanthanide (Ln) triflates were investigated as sustainable catalysts for aromatic sulfonylation reactions under microwave irradiation. The catalytic efficiency of the early triflates La(OTf)3–Eu(OTf)3 is good for long irradiation times. For the later lanthanides, yields reaching over 90 % were achieved for short irradiation periods. This was the case especially for Tm(OTf)3, Yb(OTf)3, and Lu(OTf)3, of which Yb(OTf)3 was the most efficient. The upward trend in catalytic efficiency therefore correlates with the lanthanide sequence in the periodic table. The results can be explained by the decrease in the radii of the Ln3+ ions, and the hydrolysis and water-exchanges rate within the series. The results are in agreement with the first principal property value (t1) calculated by principal component analysis (PCA) published previously. A large drop in sulfonylation yield was obtained with Gd(OTf)3, which matched the “gadolinium break”; the well-known discontinuity in lanthanide properties

    U2 - 10.1002/ajoc.201402067

    DO - 10.1002/ajoc.201402067

    M3 - Journal article

    VL - 3

    SP - 963

    EP - 968

    JO - Asian Journal of Organic Chemistry

    JF - Asian Journal of Organic Chemistry

    SN - 2193-5807

    IS - 9

    ER -