Tetrabutylammonium iodide catalyzed allylic sulfonylation of Baylis-Hillman acetates with sulfonylhydrazides in water

被引:105
|
作者
Li, Xiaoqing [1 ]
Xu, Xiangsheng [1 ]
Tang, Yucai [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL-FREE; OXIDATIVE AMINATION; RADICALS; SULFONES; DERIVATIVES; BONDS; TBHP;
D O I
10.1039/c3ob27329f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tetrabutylammonium iodide catalyzed method for the synthesis of allyl aryl sulfone derivatives with Baylis-Hillman acetates and sulfonylhydrazides using tert-butyl hydroperoxide as an oxidation agent in water has been developed. In this process, the group eliminated from the sulfonyl precursor is molecular nitrogen.
引用
收藏
页码:1739 / 1742
页数:4
相关论文
共 50 条
  • [41] Sm/HOAc/EtOH system-mediated reduction of Baylis-Hillman acetates
    Liu, Yunkui
    Mao, Daffie
    Xu, Danqian
    Xu, Zhenyuan
    Zhang, Yongmin
    SYNTHETIC COMMUNICATIONS, 2007, 37 (22-24) : 4389 - 4397
  • [42] Al/PbCl2-catalyzed DMF-mediated reductive coupling of Baylis-Hillman acetates with tetrachloromethane
    Lui, Yunkui
    Xu, Danqian
    Xu, Zhenyuan
    Zhang, Yongmin
    SYNLETT, 2007, (11) : 1671 - 1674
  • [43] Deconjugated Baylis-Hillman reactions catalyzed by small organic molecules
    Chai, Yonghai
    Chen, Yange
    Wang, Panru
    Zhang, Qi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [44] Synthesis of Spiroheterocycles by Palladium-Catalyzed Domino Cycloisomerization/Cross-Coupling of α-Allenols and Baylis-Hillman Acetates
    Alcaide, Benito
    Almendros, Pedro
    Martinez del Campo, Teresa
    Teresa Quiros, M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) : 3344 - 3346
  • [45] P-isocupreidine-catalyzed asymmetric Baylis-Hillman reactions
    Hatakeyama, Susumi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2006, 64 (11) : 1132 - 1138
  • [46] Hexamethylenetetramine-ionic liquids catalyzed Baylis-Hillman reactions
    de Souza, Rodrigo O. M. A.
    Fregadolli, Pedro H.
    Goncalves, Karen M.
    Sequeira, Lucia C.
    Pereira, Vera L. P.
    Filho, Lucio C.
    Esteves, Pierre M.
    Vasconcellos, Mario L. A. A.
    Antunes, Octavio A. C.
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (12) : 936 - 939
  • [47] Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates
    Cho, CW
    Kong, JR
    Krische, MJ
    ORGANIC LETTERS, 2004, 6 (08) : 1337 - 1339
  • [48] Asymmetric Baylis-Hillman reaction catalyzed by pyrrolidine based organocatalyst
    Menkudle, Madhavi S.
    Pendalwar, Shrikant S.
    Goswami, Santosh, V
    Jadhav, Wamanrao N.
    Bhusare, Sudhakar R.
    SN APPLIED SCIENCES, 2020, 2 (04):
  • [49] β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines
    Kawahara, S
    Nakano, A
    Esumi, T
    Iwabuchi, Y
    Hatakeyama, S
    ORGANIC LETTERS, 2003, 5 (17) : 3103 - 3105
  • [50] Lipase-catalyzed kinetic resolution of Baylis-Hillman products
    Hayashi, N
    Yanagihara, K
    Tsuboi, S
    TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3825 - 3830