Asymmetric cycloaddition of CO2 and an epoxide using recyclable bifunctional polymeric Co(III) salen complexes under mild conditions

被引:39
|
作者
Roy, Tamal [1 ]
Kureshy, Rukhsana I. [1 ,2 ]
Khan, Noor-ul H. [1 ,2 ]
Abdi, Sayed H. R. [1 ,2 ]
Bajaj, Hari C. [1 ,2 ]
机构
[1] Cent Salt & Marine Chem Res Inst CSIR CSMCRI, Discipline Inorgan Mat & Catalysis, Bhavnagar 364021, Gujarat, India
[2] CSIR, CSMCRI, Acad Sci & Innovat Res AcSIR, Bhavnagar 364021, Gujarat, India
关键词
CARBON-DIOXIDE; CYCLIC CARBONATES; PROPYLENE-OXIDE; KINETIC RESOLUTION; ORGANIC CARBONATES; TERMINAL EPOXIDES; CATALYST SYSTEMS; RACEMIC EPOXIDES; ENANTIOSELECTIVITY; COPOLYMERIZATION;
D O I
10.1039/c3cy00325f
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Bifunctional polymeric Co(III) salen complexes 1a-g derived from (1R,2R)-(-)-1,2-diaminocyclohexane and a triazine-piperazine core were synthesized and screened for the asymmetric cycloaddition reaction of CO2 and an epoxide under mild conditions. A moderate K-rel value of 11.2 for the product propylene carbonate (ee = 74%) was obtained with catalyst 1e which does not require any external base as the co-catalyst. The polymeric Co(III)-CCl3COO (1e) was efficiently recycled 10 times without any significant loss in activity under the present reaction conditions.
引用
收藏
页码:2661 / 2667
页数:7
相关论文
共 50 条
  • [1] Hydroboration of aldehydes, ketones and CO2 under mild conditions mediated by iron(iii) salen complexes
    Lau, Samantha
    Provis-Evans, Cei B.
    James, Alexander P.
    Webster, Ruth L.
    DALTON TRANSACTIONS, 2021, 50 (31) : 10696 - 10700
  • [2] Synthesis of cyclic carbonate from CO2 and epoxide using bifunctional imidazolium ionic liquid under mild conditions
    Yue, Shuang
    Wang, Pingping
    Hao, Xueying
    FUEL, 2019, 251 : 233 - 241
  • [3] Exploring the potential of group III salen complexes for the conversion of CO2 under ambient conditions
    Aomchad, Vatcharaporn
    Gobbo, Silvano Del
    Yingcharoen, Prapussorn
    Poater, Albert
    D'Elia, Valerio
    CATALYSIS TODAY, 2021, 375 : 324 - 334
  • [4] Highly recyclable and magnetic catalyst of a metalloporphyrin-based polymeric composite for cycloaddition of CO2 to epoxide
    Chen, Aibing
    Ju, Pengpeng
    Zhang, Yunzhao
    Chen, Jinzhu
    Gao, Hui
    Chen, Limin
    Yu, Yifeng
    RSC ADVANCES, 2016, 6 (99): : 96455 - 96466
  • [5] Co(III)-Salen immobilized cellulose nanocrystals for efficient catalytic CO2 fixation into cyclic carbonates under mild conditions
    Hu, Lingling
    Xie, Qiujian
    Tang, Juntao
    Pan, Chunyue
    Yu, Guipeng
    Tam, Kam Chiu
    CARBOHYDRATE POLYMERS, 2021, 256
  • [6] Metal-salen molecular cages as efficient and recyclable heterogeneous catalysts for cycloaddition of CO2 with epoxides under ambient conditions
    Ng, Chee Koon
    Toh, Ren Wei
    Lin, Ting Ting
    Luo, He-Kuan
    Hor, T. S. Andy
    Wu, Jie
    CHEMICAL SCIENCE, 2019, 10 (05) : 1549 - 1554
  • [7] Asymmetric Aminolytic Kinetic Resolution of Racemic Epoxides Using Recyclable Chiral Polymeric Co(III)-Salen Complexes: A Protocol for Total Utilization of Racemic Epoxide in the Synthesis of (R)-Naftopidil and (S)-Propranolol
    Kumar, Manish
    Kureshy, Rukhsana I.
    Shah, Arpan K.
    Das, Anjan
    Khan, Noor-ul H.
    Abdi, Sayed H. R.
    Bajaj, Hari C.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9076 - 9084
  • [8] Immobilized bifunctional phosphonium salts as recyclable organocatalysts in the cycloaddition of CO2 and epoxides
    Steinbauer, J.
    Longwitz, L.
    Frank, M.
    Epping, J.
    Kragl, U.
    Werner, T.
    GREEN CHEMISTRY, 2017, 19 (18) : 4435 - 4445
  • [9] Theoretical Study on Epoxide Ring-opening in CO2/Epoxide Copolymerization Catalyzed by Bifunctional Salen-Type Cobalt(III) Complexes: Influence of Stereoelectronic Factors
    Dyduch, Karol
    Roznowska, Aleksandra
    Srebro-Hooper, Monika
    Lee, Bun Yeoul
    Michalak, Artur
    CATALYSTS, 2021, 11 (03) : 1 - 26
  • [10] Reaction Mechanism of Epoxide Cycloaddition to CO2 Catalyzed by Salen-M (M = Co, Al, Zn)
    Wang, Ting-Ting
    Xie, Yong
    Deng, Wei-Qiao
    JOURNAL OF PHYSICAL CHEMISTRY A, 2014, 118 (39): : 9239 - 9243