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AuPd Alloys and Chiral Proline Dual-Functionalized NH2-UiO-66 Catalysts for Tandem Oxidation/Asymmetric Aldol Reactions

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Abstract

Rational design and precise engineering of a multifunctional catalyst at the molecular level to fulfill a multi-step tandem procedure still face serious challenges. Here, we first constructed two metal alloy NPs@chiral MOFs bifunctional catalysts, in which stable NH2-UiO-66 was selected as parent MOF, chiral proline was introduced via coordination to the zirconium nodes and tiny AuPd alloy NPs with the Au/Pd ratios of 3:1 and 1:3 were encapsulated into the parent MOF via “bottle-around-ship” method. The bifunctional and heterogeneous catalysts displayed excellent oxidation performance (yield up to 93%) and satisfied enantioselectivities (eeanti value up to 91%) in tandem selective oxidation of aromatic alcohol/asymmetric Aldol reactions. Control experiments showed that there was synergistic effect existed in AuPd NPs, and Au and Pd NPs played a leading and co-catalyst role, respectively, during the oxidation reactions. Macro-substrate experiment suggested that the catalytic reaction occurred inside the pores of the catalysts. The catalysts can also be recycled for at least three times without obvious activity loss and structural change.

Graphical Abstract

Alloy NPs@chiral MOFs bifunctional catalysts were first constructed, in which stable NH2-UiO-66 was selected as parent MOF, and versatile chiral proline and tiny AuPd alloy NPs were introduced as catalytic sites. They were applied to tandem oxidation/asymmetric Aldol reactions with excellent oxidation performance and satisfied enantioselectivities.

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Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Jiangsu Province (BK20131289), the Fundamental Research Funds for the Central Universities, the National Natural Science Foundation of China (No. 21471031) and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

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  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing, 211189, People’s Republic of China

    Lin Cheng, Qiaoqiao Guo, Kaiyuan Zhao, Yi-Ming Li, Hao Ren, Chun-Yan Ji & Wenjing Li

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10562_2022_4044_MOESM1_ESM.docx

Supplementary file Full instrument details, additional characterizations (FT-IR, UV–vis, and CD spectra) of the bifunctional catalysts, the data of bulk substrate and recycling tests, and 1HNMR characterization and HPLC analysis of racemates and asymmetric products. The Supporting Information is available free of charge at https://pubs.acs.org/doi/xx.xxxx/acs.inorgchem.xxxxxxx. (DOCX 1389 KB)

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Cheng, L., Guo, Q., Zhao, K. et al. AuPd Alloys and Chiral Proline Dual-Functionalized NH2-UiO-66 Catalysts for Tandem Oxidation/Asymmetric Aldol Reactions. Catal Lett 153, 1024–1035 (2023). https://doi.org/10.1007/s10562-022-04044-w

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