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Mesoporous material AlPS-BrPPAS derivatives supported chiral Mn(III) salen complex and highly efficient epoxidation of olefins as a recoverable catalyst

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Abstract

A novel layered crystalline of organic–inorganic hybrid material aluminium 3-bromopropylphosphonate-phosphate (AlPS-BrPPAS) was synthesized and used as catalyst supports for immobilization of chiral salen Mn(III) with different types of diamine linkers. The heterogeneous salen Mn(III) catalysts were characterized by FT-IR, XRD, TG, SEM, and N2 sorption, and the results indicated the successful immobilization of the chiral Mn(III) salen complex. It was found that the structure of the catalysts was closely correlated with the linkers. The confinement effect of linkers on the catalytic performance of the heterogeneous catalysts was studied for the asymmetric epoxidation of unfunctionalized olefins with sodium hypochlorite as an oxidant. Moreover, the heterogeneous chiral salen Mn(III) catalysts can be recovered and reused up to nine times with retention of conversion and enantioselectivity. Interestingly, two heterogeneous chiral salen Mn(III) catalysts with different linkers also significantly alter the configuration of epoxide products for 6-cyano-2,2-dimethylchromene and 6-nitro-2,2-dimethyl-chromene.

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Acknowledgments

This work was financially supported by National Ministry of Science and Technology Innovation Fund for High-tech Small and Medium Enterprise Technology (No. 09C26215112399) and National Ministry of Human Resources and Social Security Start-up Support Projects for Students Returned to Business, Office of Human Resources and Social Security Issued 2009 (143).

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Authors and Affiliations

  1. Gezhouba Explosive Co. Ltd., Chongqing, 401121, People’s Republic of China

    Ziyong Jia, Yun Dong, Huaping Zhao & Guisong Zhou

  2. College of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry, Southwest University, Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing, 400715, People’s Republic of China

    Xiangkai Fu

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  1. Ziyong Jia
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  2. Yun Dong
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  3. Huaping Zhao
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  4. Guisong Zhou
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  5. Xiangkai Fu
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Correspondence to Ziyong Jia.

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Jia, Z., Dong, Y., Zhao, H. et al. Mesoporous material AlPS-BrPPAS derivatives supported chiral Mn(III) salen complex and highly efficient epoxidation of olefins as a recoverable catalyst. Res Chem Intermed 41, 6169–6183 (2015). https://doi.org/10.1007/s11164-014-1730-6

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  • DOI: https://doi.org/10.1007/s11164-014-1730-6

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