Oxidative Cleavage of Silyl Ethers by an Oxoammonium Salt

被引：8
作者：
Loman, Jacob J. [1 ]
Pistritto, Vincent A. [1 ]
Kelly, Christopher B. [1 ]
Leadbeater, Nicholas E. [1 ,2 ]
机构：
[1] Univ Connecticut, Dept Chem, 55 North Eagleville Rd, Storrs, CT 06269 USA
[2] Univ Connecticut, Ctr Hlth, Dept Community Med & Hlth Care, 263 Farmington Ave, Farmington, CT 06030 USA
来源：
SYNLETT | 2016年 / 27卷 / 16期
基金：
美国国家科学基金会;
关键词：
protecting groups; silicon; oxidation; oxoammonium salt; aldehydes; ketones; DEPROTECTION; COMPLEXES; ALCOHOLS; TEMPO;
D O I：
10.1055/s-0035-1561498
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the oxidative cleavage of silyl ethers to their corresponding carbonyl species mediated by an oxoammonium salt is described. The resulting aldehydes and ketones are obtained under mild reaction conditions with no observed overoxidation. For robust substrates, heating to reflux temperatures significantly reduces the reaction time.
引用
收藏
页码：2372 / 2377
页数：6
相关论文
共 18 条
  • [1] One-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants
    Barnych, Bogdan
    Vatele, Jean-Michel
    [J]. SYNLETT, 2011, (14) : 2048 - 2052
  • [2] Oxoammonium Salt Oxidations of Alcohols in the Presence of Pyridine Bases
    Bobbitt, James M.
    Bartelson, Ashley L.
    Bailey, William F.
    Hamlin, Trevor A.
    Kelly, Christopher B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 1055 - 1067
  • [3] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
    COREY, EJ
    VENKATESWARLU, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
  • [4] Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon-Oxygen Bonds
    DiLauro, Anthony M.
    Seo, Wanji
    Phillips, Scott T.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) : 7352 - 7358
  • [5] Dinitrogen tetraoxide complexes of iron(III) and copper(II) nitrates as versatile reagents for organic syntheses. Efficient oxidative deprotection of silyl or tetrahydropyranyl ethers, acetals, and thioacetals
    Firouzabadi, H
    Iranpoor, N
    Zolfigol, MA
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (09) : 2169 - 2173
  • [6] Greene T. W., 1999, PROTECTIVE GROUPS OR
  • [7] Dehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt
    Hamlin, Trevor A.
    Kelly, Christopher B.
    Leadbeater, Nicholas E.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (18) : 3658 - 3661
  • [8] Novel method for efficient aerobic oxidation of silyl ethers to carbonyl compounds catalyzed with N-hydroxyphthalimide (NHPI) and lipophilic Co(II) complexes
    Karimi, B
    Rajabi, J
    [J]. ORGANIC LETTERS, 2004, 6 (17) : 2841 - 2844
  • [9] Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt
    Kelly, Christopher B.
    Lambert, Kyle M.
    Mercadante, Michael A.
    Ovian, John M.
    Bailey, William F.
    Leadbeater, Nicholas E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (14) : 4241 - 4245
  • [10] Oxidative cleavage of allyl ethers by an oxoammonium salt
    Kelly, Christopher B.
    Ovian, John M.
    Cywar, Robin M.
    Gosselin, Taylor R.
    Wiles, Rebecca J.
    Leadbeater, Nicholas E.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) : 4255 - 4259
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