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New reusable heterogeneous catalyst in the MPV reduction in cyclohexenones: moderate one-pot synthesis of cyclohexenols (effect of methyl substituents)

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Abstract

Inorganic compounds grafted MCM-41 catalysts and the Meerwein–Ponndorf–Verley reduction (MPV) on these heterogeneous catalysts are very attractive subject areas in chemistry. New mesoporous In(OiPr)3-MCM-41 was tested for MPV reaction of cyclohexenones. Effect of methyl substituents on cyclohexenol yield was investigated. Also, reusability of catalyst was studied. Mesoporous In(OiPr)3-MCM-41 catalyzed MPV reduction in cyclohexenones to corresponding cyclohexenols in pretty good yields. Higher reaction times and lower alcohol yields for the methyl substitute cyclohexenones were obtained with In(OiPr)3-MCM-41 compared with the non-sübstitute cyclohexenone. Methyl substitute cyclohexenones as compared with non-substitute cyclohexenone compounds have lower activities that probably resulted from steric hindrance of alkyl group. Methyl group can create steric effect for cite accessibility of the catalyst. Moreover, In(OiPr)3-MCM-41 catalyst exhibited excellent recyclability for six MPV reduction round without significant loss of the reactivity. Also, the In(OiPr)3 does not leach during the reduction reaction. Heterogeneous In(OiPr)3-MCM-41 was found as very influential catalyst for the preparation of cyclohexenol derivatives.

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Acknowledgements

We gratefully acknowledge our Scientific and Technical Research Council of Turkey (TUBITAK) for financial support of under Grant No. 113Z389. I thanks to Prof. Dr. Birsen S. Oksal for their contributions.

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  1. Department of Chemistry and Chemical Processing Technologies, Denizli Technical Sciences Vocational School, Pamukkale University, Denizli, 20160, Turkey

    Burcu Uysal Karatas

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Uysal Karatas, B. New reusable heterogeneous catalyst in the MPV reduction in cyclohexenones: moderate one-pot synthesis of cyclohexenols (effect of methyl substituents). J IRAN CHEM SOC 20, 29–36 (2023). https://doi.org/10.1007/s13738-022-02698-2

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