Construction of a Lanthanide Cage with a Hollow-Walled Cavity and Large Windows to Promote Nucleophilic Additions

Metal–organic cages (MOCs) as artificial mimic enzymes can allow small organic molecules to freely move in and out of the cavity with confined space, which often can increase intermolecular collisions and accelerate those reactions that are difficult to occur. This kind of homogeneous catalyst possesses high catalytic activity and regioselectivity, attracting growing interest recently. However, the rational design of MOCs with large openings as well as rich active sites for efficient chemical conversions remains a great challenge. Herein, we report a decanuclear 3d-4f MOC, Zn2Yb8, with a hollow-walled cavity and four large windows self-assembled cooperatively by bridging ligands, Zn-based metalloligands, and lanthanide Yb3+ ions. The lantern-like Zn2Yb8 not only exposes unblocked passageways for allowing more guest molecules to penetrate the cage smoothly but also provides rich Lewis centers within the cavity, which could promote nucleophilic additions to effectively boost Friedel–Crafts alkylation and the three-component Strecker reaction. With the Zn2Yb8 catalyst, more than 13 bis(indolyl)methane derivatives could be synthesized easily in 53–98% through Friedel–Crafts alkylation, and the conversion of the Strecker reaction for aniline, benzaldehyde, and trimethylsilyl cyanide could achieve approximately 98% in 3 h. Furthermore, host–guest relationship investigations confirmed that the catalytic function of the Zn2Yb8 cage could be mainly attributed to the synergy of the inherent confinement effect, multiple Lewis catalytic sites, and host–guest electrostatic interactions in the coordination cage. The construction of the discrete 3d-4f MOC with large windows and its catalytic applications in nucleophilic additions may represent a potential approach for developing enzyme-like supramolecular nanoreactors.

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Publication Details

Journal
Chemistry of Materials
Published
2024-10-28
DOI
https://doi.org/10.1021/acs.chemmater.4c02252
Citations
3
Primary Topic
Supramolecular Chemistry and Complexes
Type
article
Field-Weighted Citation Impact
0.75

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article

Construction of a Lanthanide Cage with a Hollow-Walled Cavity and Large Windows to Promote Nucleophilic Additions

Jingzhe Li, Weisheng Liu, Mei‐Lin Wu, Xiaoyu Huang et al.
3 citations
Chemistry of Materials
Supramolecular Chemistry and Complexes
0.75
article

Construction of a Lanthanide Cage with a Hollow-Walled Cavity and Large Windows to Promote Nucleophilic Additions

Jingzhe Li, Weisheng Liu, Mei‐Lin Wu, Xiaoyu Huang, Shengbin Zhou, Yu Tang, Xiaoliang Tang, Fan Dong, Manchang Kou
article en
3 citations

Abstract

Metal–organic cages (MOCs) as artificial mimic enzymes can allow small organic molecules to freely move in and out of the cavity with confined space, which often can increase intermolecular collisions and accelerate those reactions that are difficult to occur. This kind of homogeneous catalyst possesses high catalytic activity and regioselectivity, attracting growing interest recently. However, the rational design of MOCs with large openings as well as rich active sites for efficient chemical conversions remains a great challenge. Herein, we report a decanuclear 3d-4f MOC, Zn2Yb8, with a hollow-walled cavity and four large windows self-assembled cooperatively by bridging ligands, Zn-based metalloligands, and lanthanide Yb3+ ions. The lantern-like Zn2Yb8 not only exposes unblocked passageways for allowing more guest molecules to penetrate the cage smoothly but also provides rich Lewis centers within the cavity, which could promote nucleophilic additions to effectively boost Friedel–Crafts alkylation and the three-component Strecker reaction. With the Zn2Yb8 catalyst, more than 13 bis(indolyl)methane derivatives could be synthesized easily in 53–98% through Friedel–Crafts alkylation, and the conversion of the Strecker reaction for aniline, benzaldehyde, and trimethylsilyl cyanide could achieve approximately 98% in 3 h. Furthermore, host–guest relationship investigations confirmed that the catalytic function of the Zn2Yb8 cage could be mainly attributed to the synergy of the inherent confinement effect, multiple Lewis catalytic sites, and host–guest electrostatic interactions in the coordination cage. The construction of the discrete 3d-4f MOC with large windows and its catalytic applications in nucleophilic additions may represent a potential approach for developing enzyme-like supramolecular nanoreactors.

Chemistry of MaterialsVol. 36(21)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 32%
Supramolecular Chemistry and Complexes
0.75
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