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Polymers 2017, 9(3), 108; doi:10.3390/polym9030108

Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins

1
Department of Biological and Chemical Engineering, Chongqing University of Education, Nan’an 400067, China
2
The Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Beibei 400715, China
3
The Key Laboratory of Eco-Environments in Three Gorges Reservoir Region Ministry of Education, College of Chemistry and Chemical Engineering, Southwest University, Beibei 400715, China
4
Research Institute of Applied Chemistry, College of Chemistry and Chemical Engineering, Southwest University, Beibei 400715, China
*
Author to whom correspondence should be addressed.
Academic Editor: Marinos Pitsikalis
Received: 7 February 2017 / Revised: 3 March 2017 / Accepted: 15 March 2017 / Published: 17 March 2017
(This article belongs to the Special Issue Metal Complexes-Mediated Catalysis in Polymerization)
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Abstract

Chiral MnIII (salen) complex supported on modified ZPS-PVPA (zirconium poly(styrene-phenylvinylphosphonate)) and ZPS-IPPA (zirconium poly(styrene-isopropenyl phosphonate)) were prepared using –CH2Cl as a reactive surface modifier by a covalent grafting method. The supported catalysts showed higher chiral induction (ee: 72%–83%) compared with the corresponding homogeneous catalyst (ee: 54%) for asymmetric epoxidation of α-methylstrene in the presence of 4-phenylpyridine N-oxide (PPNO) as axial base using NaClO as an oxidant. ZPS-PVPA-based catalyst 1, with a larger pore diameter and surface area, was found to be more active than ZPS-IPPA-based catalyst 2. In addition, bulkier alkene-like indene, was efficiently epoxidized with these supported catalysts (ee: 96%–99%), the results were much higher than those for the homogeneous system (ee: 65%). Moreover, the prepared catalysts were relatively stable and can be recycled at least eight times without significant loss of activity and enantioselectivity. View Full-Text
Keywords: Chiral MnIII (salen) complex; hybrid zirconium phosphonate; covalent attachment; heterogeneous catalyst; asymmetric epoxidation Chiral MnIII (salen) complex; hybrid zirconium phosphonate; covalent attachment; heterogeneous catalyst; asymmetric epoxidation
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Zou, X.; Wang, C.; Wang, Y.; Shi, K.; Wang, Z.; Li, D.; Fu, X. Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins. Polymers 2017, 9, 108.

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