Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Aldehydes

被引：98
|
作者：
Li, Yuanming [1 ]
Jia, Fan [1 ]
Li, Zhiping [1 ,2 ]
机构：
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] China Univ Petr, State Key Lab Heavy Oil Proc, Beijing 102249, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 01期
基金：
美国国家科学基金会;
关键词：
aldehydes; amidation; amines; iron; oxidation; C-H BOND; AMIDE SYNTHESIS; N-DEMETHYLATION; DISSOCIATION ENERGIES; COUPLING REACTIONS; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; FACILE SYNTHESIS; ARYL HALIDES; ALCOHOLS;
D O I：
10.1002/chem.201203824
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unconventional couple: A new oxidative coupling protocol for amide bond formation has been developed (see scheme). The method provides an efficient and practical route for the synthesis of tertiary amides from readily available tertiary amines and aldehydes in the presence of a simple FeCl2 catalyst. Mechanistic studies indicated that a peroxide and an iminium ion act as the reactive intermediates in this oxidative amidation.
引用
收藏
页码：82 / 86
页数：5
相关论文
共 50 条
  • [1] Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids
    Ma, Lina
    Li, Yuanming
    Li, Zhiping
    [J]. SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1310 - 1315
  • [2] Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids
    Lina Ma
    Yuanming Li
    Zhiping Li
    [J]. Science China(Chemistry), 2015, 58 (08) : 1310 - 1315
  • [3] Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids
    Lina Ma
    Yuanming Li
    Zhiping Li
    [J]. Science China Chemistry, 2015, (08) : 1310 - 1315
  • [4] Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids
    Lina Ma
    Yuanming Li
    Zhiping Li
    [J]. Science China Chemistry, 2015, 58 : 1310 - 1315
  • [5] Iron-catalyzed oxidative amidation of acylhydrazines with amines
    Wang, Yi-Jie
    Zhang, Guo-Yu
    Shoberu, Adedamola
    Zou, Jian-Ping
    [J]. TETRAHEDRON LETTERS, 2021, 80
  • [6] Amide Bond Formation through Iron-Catalyzed Oxidative Amidation of Tertiary Amines with Anhydrides
    Li, Yuanming
    Ma, Lina
    Jia, Fan
    Li, Zhiping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5638 - 5646
  • [7] In situ protection and deprotection of amines for iron catalyzed oxidative amidation of aldehydes
    Bathini, Thulasiram
    Rawat, Vikas S.
    Bojja, Sreedhar
    [J]. TETRAHEDRON LETTERS, 2015, 56 (41) : 5656 - 5660
  • [8] nBu4NI-catalyzed oxidative amidation of aldehydes with tertiary amines
    Wang, Shan
    Wang, Jian
    Guo, Rui
    Wang, Gao
    Chen, Shan-Yong
    Yu, Xiao-Qi
    [J]. TETRAHEDRON LETTERS, 2013, 54 (46) : 6233 - 6236
  • [9] Iron-Catalyzed Amidation of Aldehydes with N-Chloroamines
    Porcheddu, Andrea
    De Luca, Lidia
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2949 - 2953
  • [10] The copper-catalyzed aerobic oxidative amidation of tertiary amines
    Cheng, Hui-Cheng
    Hou, Wen-Jun
    Li, Zeng-Wen
    Liu, Ming-Yu
    Guan, Bing-Tao
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (99) : 17596 - 17599
12345