Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System

被引:75
|
作者
Zhu, Mingwen [1 ]
Fujita, Ken-ichi [1 ]
Yamaguchi, Ryohei [1 ]
机构
[1] Kyoto Univ, Grad Sch Human & Environm Studies, Sakyo Ku, Kyoto 6068501, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 20期
关键词
AMIDE SYNTHESIS; MILD AMIDATION; ARYL HALIDES; CARBON-MONOXIDE; BOND FORMATION; MANNICH-BASES; THIO ACIDS; AMINATION; AMINOCARBONYLATION; COMPLEXES;
D O I
10.1021/jo301553v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and convenient CuI/2-pyridonate catalytic system for the oxidative amidation of aldehydes with secondary amines has been developed. With this system, a variety of useful arylamides have been synthesized in moderate to; good yields in the presence of small amount of copper catalyst and the pyridonate ligand, generating only water as a coproduct. Synthesis of cinnamamides was also achieved by the reactions of cinnamaldehydes with secondary amines in moderate yields. Air was successfully employed as a green oxidant in this catalytic system, achieving a safe and atom-efficient system for the synthesis of amides.
引用
收藏
页码:9102 / 9109
页数:8
相关论文
共 43 条
  • [22] A novel and efficient catalytic system for aerobic oxidative coupling of 2-naphthol derivatives
    Chen, L
    Lan, JB
    Mao, ZH
    Yu, XQ
    Xie, RG
    CHINESE CHEMICAL LETTERS, 2004, 15 (08) : 903 - 906
  • [23] Visible-Light-Induced Multicomponent Reaction of Aromatic Aldehydes, Amines and Sodium Difluoromethanesulfinate: Synthesis of CF2H-Substituted Secondary Amines
    Zhang, Shanshan
    Geng, Yang
    Jiao, Jialong
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4132 - 4137
  • [24] KO2/crown ether:: a novel catalytic system for the hydrosilation and Tishchenko reaction of aromatic aldehydes
    Le Bideau, F
    Coradin, T
    Gourier, D
    Hénique, J
    Samuel, E
    TETRAHEDRON LETTERS, 2000, 41 (27) : 5215 - 5218
  • [25] 2,2,2-Trifluoroethanol activated one-pot Mannich-like reaction of β-nitroenamines, secondary amines, and aromatic aldehydes
    Han, Li
    Feng, Yian
    Luo, Ming
    Yuan, Zihao
    Shao, Xusheng
    Xu, Xiaoyong
    Li, Zhong
    TETRAHEDRON LETTERS, 2016, 57 (25) : 2727 - 2731
  • [26] Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine
    Nagasawa, Y.
    Matsusaki, Y.
    Nobuta, T.
    Tada, N.
    Miura, T.
    Itoh, A.
    RSC ADVANCES, 2015, 5 (78): : 63952 - 63954
  • [27] Co(OAc)2/TBHP as a Highly Active Catalytic System for the Selective Oxidation of Aromatic Amines to Nitro Derivatives
    Wu, Liqiong
    Yao, Lifeng
    Yin, Weiyan
    Yu, Junxia
    SYNTHESIS-STUTTGART, 2023, 55 (19): : 3104 - 3108
  • [28] Application of the Cu(i)/TEMPO/O2 catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines
    Luo, Zheng
    Liu, Yan
    Wang, Chao
    Fang, Danjun
    Zhou, Junyu
    Hu, Huayou
    GREEN CHEMISTRY, 2019, 21 (17) : 4609 - 4613
  • [29] Synthesis and stereochemistry of chiral azetidineones-2 and azetidinethiones-2. Stereochemistry of nucleophilic catalytic addition of primary and cyclic secondary amines to esters of crotonic, metacrylic and cinnamic acids
    Romanova, NN
    Gravis, AG
    Leshcheva, IF
    Ashkinadze, LD
    Grachiova, RA
    Akatieva, ME
    Bundel, YG
    VESTNIK MOSKOVSKOGO UNIVERSITETA SERIYA 2 KHIMIYA, 1996, 37 (01): : 76 - 77
  • [30] Catalytic activity of CuI/CuII cyanide based phenanthroline-bicarbonate system for enhancing aerobic oxidation of 2,6-di-tert-butylphenol
    El-khalafy, S.
    Etaiw, S. El-din
    Hassanein, M.
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2022, 26 (03)