Chiral titanium(IV) and vanadium(V) salen complexes as catalysts for carbon dioxide and epoxide coupling reactions

被引:13
作者
Kuznetsova, Svetlana A. [1 ]
Gorodishch, Ilia, V [2 ]
Gak, Alexander S. [1 ,3 ]
Zherebtsova, Valeria V. [4 ]
Gerasimov, Igor S. [5 ]
Medvedev, Michael G. [4 ,5 ]
Kitaeva, Dinara Kh [1 ]
Khakina, Ekaterina A. [1 ]
North, Michael [6 ]
Belokon, Yuri N. [1 ]
机构
[1] Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia
[2] Moscow MV Lomonosov State Univ, Chem Dept, Leninskiye Gory 1-3, Moscow 119991, Russia
[3] Moscow MV Lomonosov State Univ, Fac Mat Sci, Leninskie Gory 1-73, Moscow 119991, Russia
[4] D Mendeleev Univ Chem Technol Russia, Russian Acad Sci, Higher Chem Coll, Zelinskogo St 38-8,80, Moscow 11733, Russia
[5] RAS, ND Zelinsky Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia
[6] Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England
基金
俄罗斯科学基金会;
关键词
Salen ligand; Carbon dioxide; Cyclic carbonate; Vanadium; Titanium; ASYMMETRIC CYANOHYDRIN SYNTHESIS; CYCLIC CARBONATES; TRIMETHYLSILYL CYANIDE; ORGANIC CARBONATES; CHEMICAL-REACTIONS; CO2; CYCLOADDITION; METAL; ORGANOCATALYSTS; ACTIVATION;
D O I
10.1016/j.tet.2021.131929
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral titanium(IV) and vanadium(V) salen complexes were found to catalyse the synthesis of cyclic carbonates from carbon dioxide and epoxides. Reactions could be conducted at room temperature and 50 bar pressure of carbon dioxide or at 100 degrees C and atmospheric pressure with catalyst concentrations as low as 0.1 mol% and co-catalyst (tetrabutylammonium bromide) concentrations as low as 0.5 mol%. The cyclic carbonates formed were racemic and a mechanism is proposed which relies on Lewis base catalysis to activate the carbon dioxide rather than Lewis acid catalysed activation of the epoxide as more commonly proposed for catalysis by metal complexes. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:10
相关论文
共 88 条
[1]   Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].
Adamo, C ;
Barone, V .
JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170
[2]   Titanium Alkoxide Complexes as Catalysts for the Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides [J].
Al-Qaisi, Feda'a ;
Streng, Emilia ;
Tsarev, Alexey ;
Nieger, Martin ;
Repo, Timo .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2015, (32) :5363-5367
[3]   Organocatalyzed coupling of carbon dioxide with epoxides for the synthesis of cyclic carbonates: catalyst design and mechanistic studies [J].
Alves, M. ;
Grignard, B. ;
Mereau, R. ;
Jerome, C. ;
Tassaing, T. ;
Detrembleur, C. .
CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (13) :2651-2684
[4]   Ascorbic Acid as a Bifunctional Hydrogen Bond Donor for the Synthesis of Cyclic Carbonates from CO2 under Ambient Conditions [J].
Arayachukiat, Sunatda ;
Kongtes, Chutima ;
Barthel, Alexander ;
Vummaleti, Sai V. C. ;
Poater, Albert ;
Wannakao, Sippakorn ;
Cavallo, Luigi ;
D'Elia, Valerio .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (08) :6392-6397
[5]   The changing paradigm in CO2 utilization [J].
Aresta, Michele ;
Dibenedetto, Angela ;
Angelini, Antonella .
JOURNAL OF CO2 UTILIZATION, 2013, 3-4 :65-73
[6]  
Bader R. F. W., 1990, ATOMS MOL QUANTUM TH
[7]   Titanocene dichloride/KI: an efficient catalytic system for synthesis of cyclic carbonates from epoxides and CO2 [J].
Bai, Dongsheng ;
Nian, Guanghui ;
Wang, Guangjian ;
Wang, Zhongzhen .
APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) :184-187
[8]   Titanocene dichloride-Lewis base: An efficient catalytic system for coupling of epoxides and carbon dioxide [J].
Bai, Dongsheng ;
Jing, Huanwang ;
Liu, Qiang ;
Zhu, Qianqian ;
Zhao, Xiaofang .
CATALYSIS COMMUNICATIONS, 2009, 11 (03) :155-157
[9]   VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates [J].
Beattie, Christopher ;
North, Michael .
RSC ADVANCES, 2014, 4 (59) :31345-31352
[10]   Titanium(salen)-Catalysed Synthesis of Di- and Trithiocarbonates from Epoxides and Carbon Disulfide [J].
Beattie, Christopher ;
North, Michael .
CHEMCATCHEM, 2014, 6 (05) :1252-1259