Highly efficient asymmetric epoxidation of olefins with a chiral manganese-porphyrin covalently bound to mesoporous SBA-15: Support effect

被引：33
作者：
Farokhi, Afsaneh [1 ]
Monfared, Hassan Hosseini [1 ]
机构：
[1] Univ Zanjan, Dept Chem, Zanjan 45195313, Iran
来源：
JOURNAL OF CATALYSIS | 2017年 / 352卷
基金：
美国国家科学基金会;
关键词：
Manganese(III)-porphyrin; Enantioselectivity; Heterogeneous catalysis; Oxidation; Mesoporous; SELECTIVE OXIDATION; CATALYTIC-ACTIVITY; SILICA; HYDROTREATMENT; ADSORPTION; MCM-41; WATER; OIL;
D O I：
10.1016/j.jcat.2017.05.014
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：
A chiral Mn-III-porphyrin complex covalently bonded with mesoporous SBA-15 (SBA15-[Mn(TCPP-R*)Cl]) was synthesized and fully characterized. The heterogeneous SBA15-[Mn(TCPP-R*)Cl] exhibited remarkable catalytic activity toward enantioselective olefin epoxidation using O-2 as terminal oxidant in the presence of isobutyraldehyde. The catalyst showed higher enantioselectivity than its homogeneous counterpart in the oxidation of alpha-methylstyrene. SBA15-[Mn(TCPP-R*)Cl] catalyzed epoxidation of styrene was achieved within 8 h and optically active styrene oxide was obtained in 89% ee and 90% yield. Likewise, styrene derivatives (trans-beta-methylstyrene, indene), conjugated cis- and trans-disubstituted olefins (e.g. cis- and tans-stilbene) and terminal olefins were converted effectively to their corresponding epoxides in 63-99% ee under the Mn(III)-catalyzed conditions. The catalyst could be recycled five times without any significant loss in activity. (C) 2017 Elsevier Inc. All rights reserved.
引用
收藏
页码：229 / 238
页数：10
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