Highly efficient asymmetric epoxidation of olefins with a chiral manganese-porphyrin covalently bound to mesoporous SBA-15: Support effect
- Resource Type
- Authors
- Afsaneh Farokhi; Hassan Hosseini Monfared
- Source
- Journal of Catalysis. 352:229-238
- Subject
- Olefin fiber
010405 organic chemistry
Enantioselective synthesis
010402 general chemistry
Heterogeneous catalysis
01 natural sciences
Catalysis
0104 chemical sciences
Styrene
chemistry.chemical_compound
chemistry
Styrene oxide
Polymer chemistry
Organic chemistry
Physical and Theoretical Chemistry
Indene
Isobutyraldehyde
- Language
- ISSN
- 0021-9517
A chiral MnIII-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 O2 as terminal oxidant in the presence of isobutyraldehyde. The catalyst showed higher enantioselectivity than its homogeneous counterpart in the oxidation of α-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-β-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.