Anhydrous Conditions Enable the Catalyst-Free Carboxylation of Aromatic Alkynes with CO2 under Mild Conditions

被引:2
作者
Toniolo, Davide [1 ]
Bobbink, Felix D. [1 ]
Dyson, Paul J. [1 ]
Mazzanti, Marinella [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
alkynes; carbon dioxide fixation; propiolic acids; C-H activation; cesium carbonate; C-H ACTIVATION; CARBON-DIOXIDE; TERMINAL ALKYNES; N-FORMYLATION; METHYLATION; MECHANISM; BONDS;
D O I
10.1002/hlca.201900258
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct carboxylation of aromatic alkynes with CO2, a cheap and widely available C1 source, is the most attractive method for the synthesis of carboxylic acids. Here we show that direct carboxylation of terminal alkynes can be simply performed in near-quantitative yield in four hours with anhydrous Cs2CO3 under mild conditions without need of a metal catalyst.
引用
收藏
页数:6
相关论文
共 32 条
  • [1] Utilisation of CO2 as a chemical feedstock:: opportunities and challenges
    Aresta, Michele
    Dibenedetto, Angela
    [J]. DALTON TRANSACTIONS, 2007, (28) : 2975 - 2992
  • [2] Intricacies of Cation-Anion Combinations in Imidazolium Salt-Catalyzed Cycloaddition of CO2 Into Epoxides
    Bobbink, Felix D.
    Vasilyev, Dmitry
    Hulla, Martin
    Chamam, Sami
    Menoud, Florent
    Laurenczy, Gabor
    Katsyuba, Sergey
    Dyson, Paul J.
    [J]. ACS CATALYSIS, 2018, 8 (03): : 2589 - 2594
  • [3] N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source
    Bobbink, Felix D.
    Das, Shoubhik
    Dyson, Paul J.
    [J]. NATURE PROTOCOLS, 2017, 12 (02) : 417 - 428
  • [4] Synthesis of carbonates and related compounds incorporating CO2 using ionic liquid-type catalysts: State-of-the-art and beyond
    Bobbink, Felix D.
    Dyson, Paul J.
    [J]. JOURNAL OF CATALYSIS, 2016, 343 : 52 - 61
  • [5] RATE AND EQUILIBRIUM STUDIES OF THE DEPROTONATION OF BENZYLIC KETONES BEARING PYRIDINIUM CATIONS
    BUNTING, JW
    STEFANIDIS, D
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (03): : 428 - 432
  • [6] Carboxylation of terminal alkynes with CO2 catalyzed by bis(amidate) rare-earth metal amides
    Cheng, Hao
    Zhao, Bei
    Yao, Yingming
    Lu, Chengrong
    [J]. GREEN CHEMISTRY, 2015, 17 (03) : 1675 - 1682
  • [7] Carbon Dioxide Capture: Prospects for New Materials
    D'Alessandro, Deanna M.
    Smit, Berend
    Long, Jeffrey R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) : 6058 - 6082
  • [8] Metal-Free Catalyst for the Chemoselective Methylation of Amines Using Carbon Dioxide as a Carbon Source
    Das, Shoubhik
    Bobbink, Felix D.
    Laurenczy, Gabor
    Dyson, Paul J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (47) : 12876 - 12879
  • [9] C-H Bond Carboxylation with Carbon Dioxide
    Hong, Junting
    Li, Man
    Zhang, Jianning
    Sun, Beiqi
    Mo, Fanyang
    [J]. CHEMSUSCHEM, 2019, 12 (01) : 6 - 39
  • [10] Delineating the Mechanism of Ionic Liquids in the Synthesis of Quinazoline-2,4(1H,3H)-dione from 2-Aminobenzonitrile and CO2
    Hulla, Martin
    Chamam, Sami M. A.
    Laurenczy, Gabor
    Das, Shoubhik
    Dyson, Paul J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) : 10559 - 10563