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
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
  • [31] Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature
    Li, Guangchen
    Szostak, Michal
    NATURE COMMUNICATIONS, 2018, 9
  • [32] Metal-free direct annulation of 2-aminophenols and 2-aminothiophenols with unactivated amides through transamidation: Access to polysubstituted benzoxazole and benzothiazole derivatives
    Kumar, Vishal
    Dhawan, Sanjeev
    Bala, Renu
    Girase, Pankaj Sanjay
    Singh, Parvesh
    Karpoormath, Rajshekhar
    TETRAHEDRON, 2022, 115
  • [33] Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature
    Guangchen Li
    Michal Szostak
    Nature Communications, 9
  • [34] Amides Activation: Transition Metal-Free Coupling Between C-N Activated Amides and Enolizable Amides
    Joseph, Devaneyan
    Oh, Min Seok
    Jayaraman, Aravindan
    Lee, Sunwoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (10) : 1293 - 1295
  • [35] Metal-Free Catalytic Formylation of Amides Using CO2 under Ambient Conditions
    Hota, Pradip Kumar
    Sau, Samaresh Chandra
    Mandal, Swadhin K.
    ACS CATALYSIS, 2018, 8 (12): : 11999 - 12003
  • [36] Metal-free one-pot synthesis of amides using graphene oxide as an efficient catalyst
    Kumari, Shweta
    Shekhar, Amiya
    Mungse, Harshal P.
    Khatri, Om P.
    Pathak, Devendra D.
    RSC ADVANCES, 2014, 4 (78): : 41690 - 41695
  • [37] Recent developments in metal-catalysed transamidation of quiescent amides
    Sakthivel, Kokila
    Ahmed, S. Shakir
    Niharan, S.
    Singh, Fateh V.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2024, 1018
  • [38] Metal-free one-pot oxidative amination of aldehydes to amides
    Ekoue-Kovi, Kekeli
    Wolf, Christian
    ORGANIC LETTERS, 2007, 9 (17) : 3429 - 3432
  • [39] Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene
    Bettinger, Holger F.
    Filthaus, Matthias
    Bornemann, Holger
    Oppel, Iris M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4744 - 4747
  • [40] α-Vinylation of amides with arylacetylenes: synthesis of allylamines under metal-free conditions
    Sun, Manman
    Wu, Huandong
    Bao, Weiliang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (41) : 7076 - 7079