Highly efficient and selective trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by polystyrene-bound tin(IV) porphyrin

被引:18
|
作者
Gharaati, Shadab [1 ,2 ]
Moghadam, Majid [1 ]
Tangestaninejad, Shahram [1 ]
Mirkhani, Valiollah [1 ]
Mohammadpoor-Baltork, Iraj [1 ]
机构
[1] Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran
[2] Payame Noor Univ, Dept Chem, Tehran, Iran
关键词
Alcohol; Phenol; Trimethylsilyl ether; Polystyrene; High-valent tin(IV) porphyrin; HIGH-VALENT METALLOPORPHYRIN; ALLYL VINYL ETHERS; HYDROXYL-GROUPS; CHEMOSELECTIVE TRIMETHYLSILYLATION; PRACTICAL PROTOCOL; O-SILYLATION; SILICA-GEL; PROTECTION; EPOXIDES; HMDS;
D O I
10.1016/j.poly.2012.01.011
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In the present work, investigation of the catalytic activity of tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn-IV(TNH2PP)(OTf)(2)]. supported on chloromethylated polystyrene in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV-Vis spectroscopic methods. This catalyst was used for selective trimethylsilylation of different alcohols and phenols with HMDS, with short reaction times and high yields. Also the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:87 / 95
页数:9
相关论文
共 50 条
  • [21] [SnIV(TPP)(BF4)2]: An efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Mohammadpoor-Baltork, Iraj
    Gharaati, Shadab
    POLYHEDRON, 2010, 29 (01) : 212 - 219
  • [22] Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL-101
    Zadehahmadi, Farnaz
    Tangestaninejad, Shahram
    Moghadam, Majid
    Mirkhani, Valiollah
    Mohammadpoor-Baltork, Iraj
    Kardanpour, Reihaneh
    APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (04) : 209 - 215
  • [23] Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) under heterogonous conditions
    Khazaei, Ardeshir
    Zolfigol, Mohammad Ali
    Rostami, Amin
    Ghorbani-Choghamarani, Arash
    CATALYSIS COMMUNICATIONS, 2007, 8 (03) : 543 - 547
  • [24] Highly Efficient Epoxidation of Alkenes with Sodium Periodate Catalyzed by Reusable Polystyrene-Bound Ruthenium(III) Salophen
    Moghadam, M.
    Mirkhani, V.
    Tangestaninejad, S.
    Mohammadpoor-Baltork, I.
    Kargar, H.
    Sheikhshoaei, I.
    Hatefi, M.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (04) : 1019 - 1029
  • [25] Highly efficient epoxidation of alkenes with sodium periodate catalyzed by reusable polystyrene-bound ruthenium(III) salophen
    M. Moghadam
    V. Mirkhani
    S. Tangestaninejad
    I. Mohammadpoor-Baltork
    H. Kargar
    I. Sheikhshoaei
    M. Hatefi
    Journal of the Iranian Chemical Society, 2011, 8 : 1019 - 1029
  • [26] ZINC-CHLORIDE CATALYZED SILYLATION OF ALCOHOLS AND PHENOLS BY HEXAMETHYLDISILAZANE - A HIGHLY CHEMOSELECTIVE REACTION
    FIROUZABADI, H
    KARIMI, B
    SYNTHETIC COMMUNICATIONS, 1993, 23 (12) : 1633 - 1641
  • [27] Efficient and selective hydrocarbon oxidation with sodium periodate under ultrasonic irradiation catalyzed by polystyrene-bound Mn (TPyP)
    Tangestaninejad, S
    Moghadam, M
    Mirkhani, V
    Kargar, H
    ULTRASONICS SONOCHEMISTRY, 2006, 13 (01) : 32 - 36
  • [28] RuIII( OTf) SalophenCH2-NHSiO2-Fe: an efficient and magnetically recoverable catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
    Torki, Maryam
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Moghadam, Majid
    Mohammadpoor-Baltork, Iraj
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (04) : 304 - 309
  • [29] High-valent tin(IV) porphyrin: An efficient and reusable catalyst for tetrahydropyranylation of alcohols and phenols under mild conditions
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Mohammadpoor-Baltork, Iraj
    Gharaati, Shadab
    INORGANICA CHIMICA ACTA, 2010, 363 (07) : 1523 - 1528
  • [30] Polystyrene-Gallium Trichloride Complex: A Mild, Highly Efficient, and Recyclable Polymeric Lewis Acid Catalyst for Chemoselective Silylation of Alcohols and Phenols with Hexamethyldisilazane
    Rahmatpour, Ali
    Vakili, Ali
    Azizian, Setare
    HETEROATOM CHEMISTRY, 2013, 24 (06) : 443 - 451