Chiral Cobalt(III) Complexes as Bifunctional BrOnsted Acid-Lewis Base Catalysts for the Preparation of Cyclic Organic Carbonates

被引:84
作者
Rulev, Yuri A. [1 ]
Larionov, Vladimir A. [1 ]
Lokutova, Anastasia V. [1 ]
Moskalenko, Margarita A. [1 ]
Lependina, Ol'ga L. [1 ]
Maleev, Victor I. [1 ]
North, Michael [2 ]
Belokon, Yuri N. [1 ]
机构
[1] AN Nesmeyanov Organoelement Cpds Inst, Moscow 19991, Russia
[2] Univ York, Dept Chem, Green Chem Ctr Excellence, York YO10 5DD, N Yorkshire, England
关键词
carbon dioxide; catalyst; cyclic carbonate; epoxide; kinetic resolution; HOMOGENEOUS CATALYST; OCTAHEDRAL COMPLEXES; CHEMICAL FIXATION; PHASE-TRANSFER; DIOXIDE; CO2; SALTS; CYCLOADDITION; EPOXIDES; SOLVENTS;
D O I
10.1002/cssc.201501365
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stereochemically inert cationic cobalt(III) complexes were shown to be one-component catalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide at 50 degrees C and 5MPa carbon dioxide pressure. The optimal catalyst possessed an iodide counter anion and could be recycled. A catalytic cycle is proposed in which the ligand of the cobalt complexes acts as a hydrogen-bond donor, activating the epoxide towards ring opening by the halide anion and activating the carbon dioxide for subsequent reaction with the halo-alkoxide. No kinetic resolution was observed when terminal epoxides were used as substrates, but chalcone oxide underwent kinetic resolution.
引用
收藏
页码:216 / 222
页数:7
相关论文
共 42 条
  • [1] [Anonymous], ANGEW CHEM
  • [2] Belokon Y. N., 2010, GREEN CHEM, V12, P1514
  • [3] Anionic chiral cobalt(III) complexes as catalysts of asymmetric synthesis of cyanohydrins
    Belokon, Yu. N.
    Maleev, V. I.
    Mal'fanov, I. L.
    Savel'eva, T. F.
    Ikonnikov, N. S.
    Bulychev, A. G.
    Usanov, D. L.
    Kataev, D. A.
    North, M.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2006, 55 (05) : 821 - 827
  • [4] A novel type of catalysts for the asymmetric C-C bond formation based on chiral stereochemically inert cationic CoIII complexes
    Belokon, Yu. N.
    Larionov, V. A.
    Mkrtchyan, A. F.
    Khrustalev, V. N.
    Nijland, A.
    Saghyan, A. S.
    Godovikov, I. A.
    Peregudov, A. S.
    Babievsky, K. K.
    Ikonnikov, N. S.
    Maleev, V. I.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2012, 61 (12) : 2252 - 2260
  • [5] Potassium and silver chiral cobaltate(III) complexes as precatalysts for asymmetric C-C bond formation
    Belokon, Yuri N.
    Maleev, Viktor I.
    Kataev, Dimitri A.
    Mal'fanov, Ilya. L.
    Bulychev, Alexander G.
    Moskalenko, Margarita A.
    Saveleva, Tat'yana F.
    Skrupskaya, Tat'yana V.
    Lyssenko, Konstantin A.
    Godovikov, Ivan A.
    North, Michael
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 822 - 831
  • [6] Chiral Octahedral Complexes of CoIII As a Family of Asymmetric Catalysts Operating under Phase Transfer Conditions
    Belokon, Yuri N.
    Maleev, Victor I.
    North, Michael
    Larionov, Vladimir A.
    Savel'yeva, Tafyana F.
    Nijland, Aike
    Nelyubina, Yuliya V.
    [J]. ACS CATALYSIS, 2013, 3 (09): : 1951 - 1955
  • [7] Chiral ion pairs in catalysis: lithium salts of chiral metallocomplex anions as catalysts for asymmetric C-C bond formation
    Belokon', Yuri N.
    Maleev, Victor I.
    Kataev, Dmitri A.
    Saveleva, Tatiana F.
    Skrupskaya, Tatiana V.
    Nelyubina, Yulia V.
    North, Michael
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1746 - 1752
  • [8] A practical route to enantiopure 1,2-aminoalcohols
    Chang, HT
    Sharpless, KB
    [J]. TETRAHEDRON LETTERS, 1996, 37 (19) : 3219 - 3222
  • [9] Quaternary onium tribromide catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides
    Chang, Tao
    Jing, Huanwang
    Jin, Lili
    Qiu, Wenyuan
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 264 (1-2) : 241 - 247
  • [10] Chiral-at-Metal Octahedral Iridium Catalyst for the Asymmetric Construction of an All-Carbon Quaternary Stereocenter
    Chen, Liang-An
    Tang, Xiaojuan
    Xi, Jianwei
    Xu, Weici
    Gong, Lei
    Meggers, Eric
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14021 - 14025