Selective C-H bond hydroxylation of cyclohexanes in water by supramolecular control

被引：7
|
作者：
Yang, Bin [1 ,2 ]
Cui, Jian-Fang [1 ,2 ]
Wong, Man Kin [1 ,2 ]
机构：
[1] Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China
来源：
RSC ADVANCES | 2017年 / 7卷 / 49期
基金：
中国国家自然科学基金;
关键词：
REGIOSELECTIVE INTRAMOLECULAR OXIDATION; GENERATED IN-SITU; BETA-CYCLODEXTRIN; ASYMMETRIC EPOXIDATION; CATALYTIC HYDROXYLATION; HYDROGEN-PEROXIDE; CHIRAL KETONES; DIOXIRANES; FUNCTIONALIZATION; NMR;
D O I：
10.1039/c7ra03930a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using beta-CD and gamma-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3- and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with beta-CD and gamma-CD in water.
引用
收藏
页码：30886 / 30893
页数：8
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