Cycloaddition of CO2 to challenging N-tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights

被引：45

作者：

Arayachukiat, Sunatda ^{[1
]}

Yingcharoen, Prapussorn ^{[1
]}

Vummaleti, Sai V. C. ^{[2
]}

Cavallo, Luigi ^{[2
]}

Poater, Albert ^{[3
,4
]}

D'Elia, Valerio ^{[1
]}

机构：

[1] Vidyasirimedhi Inst Sci & Technol VISTEC, Sch Mol Sci & Engn, Dept Mat Sci & Engn, Wang Chan 21210, Thailand

[2] King Abdullah Univ Sci & Technol, KCC, Thuwal 239556900, Saudi Arabia

[3] Univ Girona, Inst Quim Computac & Catalisi, C Maria Aurelia Capmany 6, Girona 17003, Catalonia, Spain

[4] Univ Girona, Dept Quim, C Maria Aurelia Capmany 6, Girona 17003, Catalonia, Spain

来源：

MOLECULAR CATALYSIS | 2017年 / 443卷

关键词：

Aziridines; Niobium; CO2; fixation; Catalysis; Cycloaddition of CO2; Mechanistic study; CARBON-DIOXIDE UTILIZATION; CYCLIC CARBONATES; CHEMICAL FIXATION; PROPYLENE-OXIDE; CONVERSION; EPOXIDES; OXAZOLIDINONES; CAPTURE; TRANSFORMATION; NUCLEOPHILE;

D O I：

10.1016/j.mcat.2017.10.023

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：

An efficient and facile approach to the regioselective synthesis of N-tosyloxazolidinones from the corresponding N-tosylaziridines and CO2 was developed using dual catalytic systems involving an early transition metal coordination compound as a Lewis acid and a nucleophilic cocatalyst. Among the screened Lewis acids, halogen-free niobium pentaethoxide (Nb(OEt)(5)) displayed the best catalytic activity when used in the presence of tetrabutylammonium iodide (TBAI). Systematic DFT calculations, supported by catalytic experiments, demonstrate that CO2 insertion is the rate determining step for this process and it is highly dependent on the steric hindrance at the niobium center. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：280 / 285

页数：6

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