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Synthesis, characterization and catalytic performance in enantioselective reactions by mesoporous silica materials functionalized with chiral thiourea-amine ligand

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Abstract

Chiral heterogeneous catalysts have been synthesized by grafting of silyl derivatives of (1R, 2R)- or (1S, 2S)-1,2-diphenylethane-1,2-diamine on SBA-15 mesoporous support. The mesoporous material SBA-15 and so-prepared chiral heterogeneous catalysts were characterized by a combination of different techniques such as X-ray diffractometry (XRD), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), field emission scanning electron microscopy (FESEM), and Brunauer–Emmett–Teller (BET) surface area. Results showed that (1R, 2R)- and (1S, 2S)-1,2-diphenylethane-1,2-diamine were successively immobilized on SBA-15 mesoporous support. Chiral heterogeneous catalysts and their homogenous counterparts were tested in enantioselective transfer hydrogenation of aromatic ketones and enantioselective Michael addition of acetylacetone to β-nitroolefin derivatives. The catalysts demonstrated notably high catalytic conversions (up to 99%) with moderate enantiomeric excess (up to 30% ee) for the heterogeneous enantioselective transfer hydrogenation. The catalytic performances for enantioselective Michael reaction showed excellent activities (up to 99%) with poor enantioselectivities. Particularly, the chiral heterogeneous catalysts could be readily recycled for Michael reaction and reused in three consecutive catalytic experiments with no loss of catalytic efficacies.

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The data that support the findings of this study are available in the supplementary material of this article.

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Acknowledgements

Mert AKGÜN from Science and Technology Application and Research Centre, Çanakkale Onsekiz Mart University, is gratefully acknowledged for his technical assistance. The authors would like to thank İrem Tutkum Aykut for her assistance during GC measurements.

Funding

This work was supported by The Scientific and Technological Research Council of Turkey (TÃœBÄ°TAK, project no: KBAG-118Z523).

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Authors and Affiliations

  1. Department of Biomedical Engineering, Bucak Faculty of Technology, Burdur Mehmet Akif Ersoy University, 15300, Bucak/Burdur, Turkey

    Yaşar Gök & Halil Zeki Gök

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  1. Yaşar Gök
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  2. Halil Zeki Gök
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YG is responsible for conceptualization, project administration, visualization, investigation, writing—review & editing, funding acquisition, supervision. HZG is responsible for methodology, investigation, writing—original Draft, conceptualization, resources and data curation.

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Correspondence to Yaşar Gök.

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Gök, Y., Gök, H.Z. Synthesis, characterization and catalytic performance in enantioselective reactions by mesoporous silica materials functionalized with chiral thiourea-amine ligand. Res Chem Intermed 47, 853–874 (2021). https://doi.org/10.1007/s11164-020-04301-w

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