Copper-catalyzed synthesis of α,β-unsaturated acylamides via direct amidation from cinnamic acids and N-substituted formamides

被引:14
|
作者
Yan, Hong [1 ]
Yang, Hailong [1 ]
Lu, Linhua [1 ]
Liu, Defu [1 ]
Rong, Guangwei [1 ]
Mao, Jincheng [1 ]
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
关键词
Amidation; Cinnamamide; N-Substituted formamide; Ligand-free; Cinnamic acid; MONOXIDE-FREE AMINOCARBONYLATION; ASYMMETRIC EPOXIDATION; AMIDES; ARYL; DERIVATIVES; CYCLIZATION; GENERALIST; EFFICIENT; RADICALS; ALPHA;
D O I
10.1016/j.tet.2013.06.078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly effective synthesis of alpha,beta-unsaturated acylamides is reported for the first time via copper-catalyzed direct amidation between readily available cinnamic acids and N-substituted formamides. The protocol was easily accessible and practical. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7258 / 7263
页数:6
相关论文
共 50 条
  • [1] Ru-catalyzed direct amidation of carboxylic acids with N-substituted formamides
    Bi, Xiaojing
    Li, Junchen
    Shi, Enxue
    Wang, Hongmei
    Gao, Runli
    Xiao, Junhua
    TETRAHEDRON, 2016, 72 (50) : 8210 - 8214
  • [2] Copper-Catalyzed Amidation of Acids Using Formamides as the Amine Source
    Xie, Ye-Xiang
    Song, Ren-Jie
    Yang, Xu-Heng
    Xiang, Jian-Nan
    Li, Jin-Heng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) : 5737 - 5742
  • [3] Copper-catalyzed decarboxylative stereospecific amidation of cinnamic acids with N-fluorobenzenesulfonimide
    Yang, Daoshan
    Sun, Mingyang
    Wei, Wei
    Li, Jin
    Sun, Pengfei
    Zhang, Qingyun
    Tian, Laijin
    Wang, Hua
    RSC ADVANCES, 2016, 6 (76): : 72361 - 72365
  • [4] Copper-catalyzed amide bond formation from formamides and carboxylic acids
    Liu, Hong-Qiang
    Liu, Jun
    Zhang, Yang-Hui
    Shao, Chang-Dong
    Yu, Jing-Xun
    CHINESE CHEMICAL LETTERS, 2015, 26 (01) : 11 - 14
  • [5] Direct Amidation of Alcohols with N-Substituted Formamides under Transition-Metal-Free Conditions
    Xu, Kun
    Hu, Yanbin
    Zhang, Sheng
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (32) : 9793 - 9797
  • [6] Copper-Catalyzed Synthesis of 2-Unsubstituted, N-Substituted Benzimidazoles
    Hirano, Keiichi
    Biju, Akkattu T.
    Glorius, Frank
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) : 9570 - 9572
  • [7] Copper-Catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide
    Wang, Sichang
    Ni, Zhangqin
    Huang, Xin
    Wang, Jichao
    Pan, Yuanjiang
    ORGANIC LETTERS, 2014, 16 (21) : 5648 - 5651
  • [8] Copper-catalyzed oxidative condensation of α-oxocarboxylic acids with formamides: synthesis of α-ketoamides
    Wang, Hua
    Guo, Li-Na
    Duan, Xin-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (28) : 4573 - 4576
  • [9] Synthesis of Substituted 2-Amino-1,3-oxazoles via Copper-Catalyzed Oxidative Cyclization of Enamines and N,N-Dialkyl Formamides
    Gao, Peng
    Wang, Juan
    Bai, Zijing
    Yang, Desuo
    Fan, Ming-Jin
    Guan, Zheng-Hui
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (15) : 1865 - 1868
  • [10] Copper-catalyzed amide bond formation from formamides and carboxylic acids
    Hong-Qiang Liu
    Jun Liu
    Yang-Hui Zhang
    Chang-Dong Shao
    Jing-Xun Yu
    Chinese Chemical Letters, 2015, 26 (01) : 11 - 14