Merging Sustainability with Organocatalysis in the Formation of Organic Carbonates by Using CO2 as a Feedstock

被引:294
作者
Whiteoak, Christopher J. [1 ]
Nova, Ainara [1 ]
Maseras, Feliu [1 ,2 ]
Kleij, Arjan W. [1 ,3 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain
[3] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
关键词
carbon dioxide fixation; cooperative effects; cycloaddition; organocatalysis; phenols; CYCLIC CARBONATES; POLARIZATION FUNCTIONS; CHEMICAL FIXATION; IONIC LIQUIDS; HYDROGEN-BOND; DIOXIDE; EFFICIENT; EPOXIDES; CATALYST; MILD;
D O I
10.1002/cssc.201200255
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The use of phenolic compounds as organocatalysts is discussed in the context of the atom-efficient cycloaddition of carbon dioxide to epoxides, forming useful cyclic organic carbonate products. The presence and cooperative nature of adjacent phenolic groups in the catalyst structure results in significantly enhanced catalytic efficiencies, allowing these CO2 fixation reactions to operate efficiently under virtually ambient conditions. The cooperative effect has also been studied by computational methods. Furthermore, when the cycloaddition reactions are carried out on a larger scale and under solvent-free conditions, further enhancements in activity are observed, combined with the advantageous requirement of reduced loadings of the binary organocatalyst system. The reported system is among one of the mildest and most effective metal-free catalysts for this conversion and contributes to a much more sustainable development of organic carbonate production; this feature has not been the main focus of previous contributions in this area.
引用
收藏
页码:2032 / 2038
页数:7
相关论文
共 64 条
  • [61] Lewis Basic Ionic Liquids-Catalyzed Conversion of Carbon Dioxide to Cyclic Carbonates
    Yang, Zhen-Zhen
    He, Liang-Nian
    Miao, Cheng-Xia
    Chanfreau, Sebastien
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2233 - 2240
  • [62] Synthesis of 5-vinylideneoxazolidin-2-ones by DBU-mediated CO2-fixation reaction of 4-(benzylamino)-2-butynyl carbonates and benzoates
    Yoshida, Masahiro
    Komatsuzaki, Yuki
    Ihara, Masataka
    [J]. ORGANIC LETTERS, 2008, 10 (10) : 2083 - 2086
  • [63] CO2 adducts of N-heterocyclic carbenes:: Thermal stability and catalytic activity toward the coupling of CO2 with epoxides
    Zhou, Hui
    Zhang, Wen-Zhen
    Liu, Cui-Hua
    Qu, Jing-Ping
    Lu, Xiao-Bing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) : 8039 - 8044
  • [64] SYNTHESIS OF POLYSILOXANES BEARING CYCLIC CARBONATE SIDE-CHAINS - DIELECTRIC-PROPERTIES AND IONIC CONDUCTIVITIES OF LITHIUM TRIFLATE COMPLEXES
    ZHU, ZY
    EINSET, AG
    YANG, CY
    CHEN, WX
    WNEK, GE
    [J]. MACROMOLECULES, 1994, 27 (15) : 4076 - 4079