Asymmetric Hydrosilation of Aromatic Ketones Catalyzed by CuFe2O4 Nanoparticles

被引:0
作者
Zhu Jielian [1 ]
Xia Xiaofeng [1 ]
Liang Minting [1 ]
Liu Xiang [1 ]
Li Hexing [2 ]
机构
[1] Jiangnan Univ, Sch Chem & Mat Engn, Minist Educ, Key Lab Food Colloids & Biotechnol, Wuxi 214122, Peoples R China
[2] Shanghai Normal Univ, Chinese Minist Educ Resource Chem, Key Lab, Shanghai 200234, Peoples R China
来源
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2016年 / 37卷 / 03期
基金
中国国家自然科学基金;
关键词
Asymmetric hydrosilation; Aromatic ketone; CeFe2O4; nanoparticles; Polymethylhydrosiloxane; EFFICIENT ENANTIOSELECTIVE HYDROSILYLATION; ARYL; HYDROGENATION; REDUCTION; EVOLUTION; AIR;
D O I
10.7503/cjcu20150650
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CuFe2O4 nanoparticles were synthesized by coprecipitation, sol. gel and solvothermal methods, respectively. The asymmetric hydrosilation of aromatic ketones was catalyzed by CuFe2O4 nanoparticles, employing (R). BINAP[2,2'-bis(diphenylphosphino)-1,1'-binaphthalene] as chiral ligand and polymethylhydrosiloxane as hydrosilating reagent. The results showed that compared to the others, the CuFe2O4 nanoparticles prepared by solvothermal method had spherical shape, small size, better dispersion, uniform distribution and excellent catalytic activities. Meanwhile, it was found that the catalytic activity of the CuFe2O4 nanoparticles was significantly improved with the addition of t-BuOK and t-BuOH. An efficient heterogeneous catalytic system CuFe2O4/t-BuOK/t-BuOH was finally obtained. Under room temperature and air atmosphere, the conversion of the aromatic ketones and the enantiomeric excesses of the (R)-1-arylethanols were up to 99% and 92%, respectively, with the heterogeneous catalytic system. It was also confirmed that the electronic effect and steric hindrance of the groups on the aromatic ring distinctly affected the results of hydrosilation. And a possible mechanism was presented to explain the influence of some key factors on the reaction. Furthermore, it was demonstrated that the CuFe2O4 nanocatalyst could be easily separated from reaction system under an external magnetic field. And after recycling for four times, the catalyst could also have a high catalytic activity for the asymmetric hydrosilation.
引用
收藏
页码:539 / 545
页数:7
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