MCM-41-supported phosphotungstic acid-catalyzed cleavage of C-O bond in allyl aryl ethers

被引:14
|
作者
Sakate, Sachin S. [1 ,2 ]
Kamble, Sumit B. [1 ]
Chikate, Rajeev C. [3 ]
Rode, Chandrashekhar V. [1 ]
机构
[1] CSIR, Natl Chem Lab, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[2] PE Soc Modern Coll Arts Sci & Commerce, Pune 411005, Maharashtra, India
[3] ME Soc Abasaheb Garware Coll, Karve Rd, Pune 411004, Maharashtra, India
关键词
CARBOHYDRATE-CHEMISTRY; SELECTIVE CLEAVAGE; PROTECTING GROUP; DODECATUNGSTOPHOSPHORIC ACID; REDUCTIVE DEPROTECTION; SAMARIUM(II) IODIDE; NEUTRAL CONDITIONS; MOLECULAR-SIEVES; TERT-BUTYLATION; ALCOHOLS;
D O I
10.1039/c7nj00375g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Removal of the protecting allyl group from allyl aryl ethers in the presence of other oxygen protecting groups was successfully achieved using a solid acid supported on the high surface area material MCM-41. The catalyst showed excellent activity in the presence of various electron withdrawing, electron donating, and oxidizable functional groups. The methodology is also very useful for the removal of protecting allyl groups of various natural products such as vanillin, isovanillin, and other oxygen functionalized aldehydes and ketones.
引用
收藏
页码:4943 / 4949
页数:7
相关论文
共 50 条
  • [1] C-O BOND-CLEAVAGE OF ALLYL ETHERS BY RHODIUM COMPOUNDS
    WAYAKU, M
    KANEDA, K
    IMANAKA, T
    TERANISHI, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (06) : 1957 - 1958
  • [2] Recent Advances in C-O Bond Cleavage of Aryl, Vinyl, and Benzylic Ethers
    Li, Pengfei
    Zhang, Mingyu
    Zhang, Lei
    TOPICS IN CURRENT CHEMISTRY, 2024, 382 (04)
  • [3] Arene Activation at Iridium Facilitates C-O Bond Cleavage of Aryl Ethers
    Miller, Alexander J. M.
    Kaminsky, Werner
    Goldberg, Karen I.
    ORGANOMETALLICS, 2014, 33 (05) : 1245 - 1252
  • [4] Arene activation promotes C-O bond cleavage in aryl alkyl ethers
    Miller, Alexander J. M.
    Goldberg, Karen I.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [5] Intermolecular Lewis acid-catalyzed cycloaddition reactions of epoxides proceeding with C-O bond cleavage
    Combee, Logan
    Shuler, William
    Falk, Isaac
    Hilinski, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [6] The mechanism of photochemical C-O or C-S bond cleavage in aryl(thio)ethers
    Inst. fur Phys. und Theor. Chem., Tech. Universität Braunschweig, Hans-Sommer Str. 10, D-38106 Braunschweig, Germany
    不详
    不详
    J. Photochem. Photobiol. A Chem., 1 (41-49):
  • [7] The mechanism of photochemical C-O or C-S bond cleavage in aryl(thio)ethers
    Pohlers, G
    Dreeskamp, H
    Grimme, S
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 95 (01) : 41 - 49
  • [8] Highly selective bimetallic FeMoP catalyst for C-O bond cleavage of aryl ethers
    Rensel, Dallas J.
    Rouvimov, Sergei
    Gin, Megan E.
    Hicks, Jason C.
    JOURNAL OF CATALYSIS, 2013, 305 : 256 - 263
  • [9] Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds
    Zeng, Xiaoqin
    Zhang, Yuxuan
    Liu, Zhengli
    Geng, Shasha
    He, Yun
    Feng, Zhang
    ORGANIC LETTERS, 2020, 22 (08) : 2950 - 2955
  • [10] Electrochemical studies on the nickel-catalyzed O-C(allyl) bond cleavage of allyl ethers
    Olivero, S
    Rolland, JP
    Duñach, E
    Labbé, E
    ORGANOMETALLICS, 2000, 19 (14) : 2798 - 2804