Copper-catalyzed protodecarboxylation of aromatic carboxylic acids

被引:177
|
作者
Goossen, Lukas J. [1 ]
Thiel, Werner R. [1 ]
Rodriguez, Nuria [1 ]
Linder, Christophe [1 ]
Melzer, Bettina [1 ]
机构
[1] Tech Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany
关键词
arenes; carboxylic acids; catalysis; copper; decarboxylation; DECARBOXYLATION; MECHANISMS; INITIO;
D O I
10.1002/adsc.200700223
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A catalyst generated from copper(I) oxide and 4,7-diphenyl-1,10-phenanthroline for the first time allows the catalytic protodecarboxylation even of deactivated aromatic carboxylic acids, giving rise to the corresponding arenes. Based on DFT calculations, a reaction pathway is proposed that accurately reflects the experimental results, such as the observed reactivity order of the substrates.
引用
收藏
页码:2241 / 2246
页数:6
相关论文
共 50 条
  • [31] Enantioenriched Allylesters via a Copper-Catalyzed Diene Carboesterification with Alkyltrifluoroborates and Carboxylic Acids
    Kennedy-Ellis, Jonathan J.
    Kelleher, Alexis D.
    Sayeed, Jaffer A.
    Burde, Ameya S.
    Chemler, Sherry R.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 1256 - 1263
  • [32] Copper-Catalyzed Carboxylation of Alkenylzirconocenes with Carbon Dioxide Leading to α,β-Unsaturated Carboxylic Acids
    Wang, Sheng
    Shao, Peng
    Chen, Chao
    Xi, Chanjuan
    ORGANIC LETTERS, 2015, 17 (20) : 5112 - 5115
  • [33] Mechanism of silver- and copper-catalyzed decarboxylation reactions of aryl carboxylic acids
    Xue, Liqin
    Su, Weiping
    Lin, Zhenyang
    DALTON TRANSACTIONS, 2011, 40 (44) : 11926 - 11936
  • [34] Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles
    Li, Yi
    Shang, Jia-Qi
    Wang, Xiang-Xiang
    Xia, Wen-Jin
    Yang, Tao
    Xin, Yangchun
    Li, Ya-Min
    ORGANIC LETTERS, 2019, 21 (07) : 2227 - 2230
  • [35] Copper-catalyzed fluoroalkylation of alkynes, and alkynyl & vinyl carboxylic acids with fluoroalkyl halides
    Ma, Jing-Jing
    Yi, Wen-Bin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) : 4295 - 4299
  • [36] Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides
    Li, Huamin
    Pan, Changduo
    Cheng, Yixiang
    Zhu, Chengjian
    TETRAHEDRON LETTERS, 2013, 54 (49) : 6679 - 6681
  • [37] Copper-Catalyzed Decarboxylative Cross-Coupling of Carboxylic Acids and Arylcarbamoyl Chlorides
    Zhou, Dun
    Fan, Aihong
    Li, Xiang
    Chen, Chunxia
    Sun, Peng
    Peng, Jinsong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (03) : 1146 - 1152
  • [38] Copper-catalyzed acyloxylation of aromatic halides
    Barrios-Landeros, Fabiola
    Ben-Zvi, Benjamin
    Kessler, Abraham
    Goodman, Brian
    Drory, David
    Levine, Dov
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [39] Preparation of aromatic amines by copper-catalyzed coupling of boronic acids with aqueous ammonia
    Jiang, Zhaoqiong
    Wu, Zhiqing
    Wang, Lixia
    Wu, Di
    Zhou, Xiangge
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2010, 88 (09): : 964 - 968
  • [40] Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines
    Wolf, C
    Liu, SL
    Mei, XF
    August, AT
    Casimir, MD
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08): : 3270 - 3273