Metal-Free Transamidation of Primary Amides using Trimethylsilyl Chloride

被引：19
|
作者：
Yu, Subeen [1 ]
Song, Kwang Ho [2 ]
Lee, Sunwoo [1 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea
[2] Korea Univ, Dept Chem & Biol Engn, Seoul 02841, South Korea
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 09期
基金：
新加坡国家研究基金会;
关键词：
transamidation; metal-free chemistry; amides; amines; trimethylsilyl chloride; CATALYZED TRANSAMIDATION; EFFICIENT CATALYST; CARBOXYLIC-ACIDS; SECONDARY AMIDES; CARBOXAMIDES; AMINES; SOLVENT; UREAS; COMPLEX;
D O I：
10.1002/ajoc.201900216
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free transamidation of primary amides was developed. Trimethylsilyl chloride (TMSCl) acted as the activator in transamidation. In the presence of TMSCl, primary amides reacted with primary amines to yield transamidated secondary amides in NMP solvent. The transamidation of benzamide with secondary amines for the formation of tertiary amides succeeds in an NMP/CHCl3 solvent mixture.
引用
收藏
页码：1613 / 1616
页数：4
相关论文
共 50 条
  • [41] Transition Metal-Free Cycloisomerization of Propargylic Amides to Oxazoles in Hexafluoroisopropanol (HFIP)
    Jankowski, Nicholas
    Dietrich, Julian
    Krause, Norbert
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (19) : 3404 - 3409
  • [42] An Umpolung Route to Amides from α-Aminonitriles under Metal-Free Conditions
    Swetha, Sathyendran
    Senadi, Gopal Chandru
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) : 2872 - 2882
  • [43] Metal-Free Formation of 2-Substitued Benzoxazoles with Amides and Esters
    Li, Fangshao
    Xiao, Jing
    Wu, Xiaofang
    Wang, Xiaoyi
    Deng, Jinfeng
    Tang, Zilong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (06) : 1778 - 1785
  • [44] Efficient and practical transition metal-free catalytic hydration of organonitriles to amides
    Tu, Tao
    Wang, Zhixun
    Liu, Zelong
    Feng, Xike
    Wang, Qingyi
    GREEN CHEMISTRY, 2012, 14 (04) : 921 - 924
  • [45] Metal-Free N-Arylation of Secondary Amides at Room Temperature
    Tinnis, Fredrik
    Stridfeldt, Elin
    Lundberg, Helena
    Adolfsson, Hans
    Olofsson, Berit
    ORGANIC LETTERS, 2015, 17 (11) : 2688 - 2691
  • [46] Metal-Free C–H Alkyliminylation and Acylation of Alkenes with Secondary Amides
    Pei-Qiang Huang
    Ying-Hong Huang
    Hui Geng
    Jian-Liang Ye
    Scientific Reports, 6
  • [47] tert-Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions
    Sureshbabu, Popuri
    Azeez, Sadaf
    Chaudhary, Priyanka
    Kandasamy, Jeyakumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (04) : 845 - 850
  • [48] Transition metal-free direct trifluoromethylthiolation of indoles using trifluoromethanesulfonyl chloride in the presence of triphenylphosphine
    Lu, Kui
    Deng, Zhijie
    Li, Ming
    Li, Tianjiao
    Zhao, Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (05) : 1254 - 1260
  • [49] Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: integrating nucleophilicity with Lewis acidic activation
    Bhunia, Mrinal
    Sahoo, Sumeet Ranjan
    Das, Arpan
    Ahmed, Jasimuddin
    Sreejyothi, P.
    Mandal, Swadhin K.
    CHEMICAL SCIENCE, 2020, 11 (07) : 1848 - 1854
  • [50] Practical povidone iodine catalyzed transamidation from primary amides and amines
    Wang, Jian
    Ren, Jiangmeng
    Zhu, Yun-Peng
    Sun, Xue-Qin
    Hu, Peng -Fei
    Mu, Xin
    Zeng, Bu -Bing
    TETRAHEDRON LETTERS, 2023, 116
12345