An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide

被引:114
|
作者
Jana, Umasish [1 ]
Maiti, Sukhendu [1 ]
Biswas, Srijit [1 ]
机构
[1] Jadavpur Univ, Dept Chem, Kolkata 700032, India
关键词
ferric chloride; amidation reactions; alcohols; atom-economical; inexpensive;
D O I
10.1016/j.tetlet.2007.11.176
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, inexpensive, environmentally friendly and high yielding amidation reaction of benzylic and allylic alcohols with primary amides using a catalytic amount of FeCl3 (5 mol %) is described. Direct substitution of various amides such as benzamide, sulfonamide, acetamide and acrylamide is reported, and this method also works on a large scale in high yield. (C) 2007 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码:858 / 862
页数:5
相关论文
共 20 条
  • [1] Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides
    Lin, Xufeng
    Wang, Jun
    Xu, Fangxi
    Wang, Yanguang
    JOURNAL OF CHEMICAL RESEARCH, 2009, (10) : 638 - 641
  • [2] A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
    Jana, Umasish
    Biswas, Srijit
    Maiti, Sukhendu
    TETRAHEDRON LETTERS, 2007, 48 (23) : 4065 - 4069
  • [3] A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols
    Zhan, Zhuang-ping
    Yu, Jing-liang
    Liu, Hui-juan
    Cui, Yuan-yuan
    Yang, Rui-feng
    Yang, Wen-zhen
    Li, Jun-ping
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21): : 8298 - 8301
  • [4] Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions
    Azizi, Mohamed Salah
    Edder, Youssef
    Karim, Abdallah
    Sauthier, Mathieu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (22) : 3796 - 3803
  • [5] FeCl3-catalyzed oxidative amidation of benzylic C-H bonds enabled by a photogenerated chlorine-radical
    Yang, Yingying
    Yu, Xianglin
    He, Na
    Huang, Xinxiang
    Song, Xizhong
    Chen, Jingbo
    Lin, Jun
    Jin, Yi
    CHEMICAL COMMUNICATIONS, 2023, 59 (68) : 10299 - 10302
  • [6] FeCl3-Catalyzed Cascade Reaction: An Efficient Approach to Functionalized Coumarin Derivatives
    He, Xinwei
    Yan, Zhenglei
    Hu, Xiaoqian
    Zuo, Yin
    Jiang, Chang
    Jin, Lei
    Shang, Yongjia
    SYNTHETIC COMMUNICATIONS, 2014, 44 (10) : 1507 - 1514
  • [7] Solvent-Free Amination of Secondary Benzylic Alcohols with N-Nucleophiles Catalyzed by FeCl3
    Yu, Jian-Jun
    Wang, Li-Min
    Guo, Feng-Lou
    Liu, Jin-Qian
    Liu, Ying
    Jiao, Ning
    SYNTHETIC COMMUNICATIONS, 2011, 41 (11) : 1609 - 1616
  • [8] Efficient deconstruction of Chinese silvergrass by FeCl3-catalyzed γ-valerolactone/water system under mild reaction condition
    Xin, Donglin
    Hu, Erling
    Zhang, Junhua
    Ran, Ganqiao
    Shi, Qingshan
    Xie, Xiaobao
    INDUSTRIAL CROPS AND PRODUCTS, 2021, 165
  • [9] Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
    Rokade, Balaji V.
    Gadde, Karthik
    Prabhu, Kandikere Ramaiah
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (12) : 2706 - 2717
  • [10] Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols
    He, Xinwei
    Shang, Yongjia
    Zhou, Yao
    Yu, Zhiyu
    Han, Guang
    Jin, Wenjing
    Chen, Jiaojiao
    TETRAHEDRON, 2015, 71 (05) : 863 - 868