Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides

被引:1
|
作者
Zhou, Dun [1 ]
Fan, Aihong [1 ]
Li, Xiang [1 ]
Chen, Chunxia [1 ]
Sun, Peng [1 ]
Peng, Jinsong [1 ]
机构
[1] Northeast Forestry Univ, Coll Chem Chem Engn & Resource Utilizat, Harbin 150040, Peoples R China
关键词
copper-catalysis; decarboxylative cross-coupling; C=C bond formation; arylcarbamoyl chloride; amide; CARBAMOYL CHLORIDES; AMIDE BOND; ALKOXYCARBONYLATION; OLEFINATION; AMINO;
D O I
10.6023/cjoc202007071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ligand-free copper-catalyzed decarboxylative cross-coupling reaction of carboxylic acids and carbamoyl chlorides in the absence of base was developed. With CuCl2 as the catalyst, the decarboxylative cross-coupling process could be realized in benzene at 120 degrees C in 48 h. Under the standard condition, the catalytic system had good functional group tolerance, and diverse amides were obtained in good to high yields. The structures of products were elucidated by H-1 NMR, C-13 NMR and HRMS spectra.
引用
收藏
页码:1146 / 1152
页数:7
相关论文
共 41 条
  • [1] Air-Stable Secondary Phosphine Oxide as Preligand for Palladium-Catalyzed Intramolecular α-Arylations with Chloroarenes
    Ackermann, Lutz
    Vicente, Ruben
    Hofmann, Nora
    [J]. ORGANIC LETTERS, 2009, 11 (19) : 4274 - 4276
  • [2] Carbonylation of C-N Bonds in Tertiary Amines Catalyzed by Low-Valent Iron Catalysts
    Allah, Tawfiq Nasr
    Savourey, Solene
    Berthet, Jean-Claude
    Nicolas, Emmanuel
    Cantat, Thibault
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) : 10884 - 10887
  • [3] PALLADIUM-CATALYZED CARBAMOYLATION AND ALKOXYCARBONYLATION OF VINYLORGANOTINS AND ARYLORGANOTINS - AN EASY ENTRY INTO VINYL OR ARYL AMIDES AND ESTERS
    BALAS, L
    JOUSSEAUME, B
    SHIN, H
    VERLHAC, JB
    WALLIAN, F
    [J]. ORGANOMETALLICS, 1991, 10 (01) : 366 - 368
  • [4] Aminolysis of Aryl Ester Using Tertiary Amine as Amino Donor via C-O and C-N Bond Activations
    Bao, Yong-Sheng
    Zhaorigetu, Bao
    Agula, Bao
    Baiyin, Menghe
    Jia, Meilin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02): : 803 - 808
  • [5] New approaches for decarboxylative biaryl coupling
    Baudoin, Olivier
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1373 - 1375
  • [6] Computer-aided rational drug design: A novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block akt signaling
    Chao, Wan-Ru
    Yean, Dawn
    Amin, Khalid
    Green, Carol
    Jong, Ling
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (15) : 3412 - 3415
  • [7] A Novel Mode of Reactivity for Gold(I): The Decarboxylative Activation of (Hetero) Aromatic Carboxylic Acids
    Cornella, Josep
    Rosillo-Lopez, Martin
    Larrosa, Igor
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) : 1359 - 1366
  • [8] Silver-catalysed protodecarboxylation of ortho-substituted benzoic acids
    Cornella, Josep
    Sanchez, Carolina
    Banawa, David
    Larrosa, Igor
    [J]. CHEMICAL COMMUNICATIONS, 2009, (46) : 7176 - 7178
  • [9] MASS SPECTRAL STUDIES .3. FRAGMENTATION OF AROMATIC AMIDES
    DAS, KG
    FUNKE, PT
    BOSE, AK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) : 3729 - &
  • [10] Nonclassical Routes for Amide Bond Formation
    de Figueiredo, Renata Marcia
    Suppo, Jean-Simon
    Campagne, Jean-Marc
    [J]. CHEMICAL REVIEWS, 2016, 116 (19) : 12029 - 12122