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A Strong‐Acid‐Resistant [Th<sub>6</sub>] Cluster‐Based Framework for Effectively and Size‐Selectively Catalyzing Reductive Amination of Aldehydes with <i>N</i>,<i>N</i>‐Dimethylformamide

Xuerui Tian, Zhiyu Jiang, Sheng‐Li Hou, Han‐Shi Hu, Jun Li, Bin Zhao

2023Angewandte Chemie International Edition24 citationsDOI

Abstract

Abstract Utilization of N,N‐dimethylformamide (DMF) as an amine source and reductant for synthesizing tertiary amines is a promising way to replace the substrates formaldehyde and dimethylamine, and it is desirable to seek porous acid‐resistant catalysts for heterogeneous catalysis of this reaction. Herein, a robust metal–organic framework (MOF) {[Th 6 O 4 (OH) 4 (H 2 O) 6 (BCP) 3 ]⋅10 DMF} n ( 1 ) containing stacked nanocages with a diameter of 1.55 nm was constructed. Compound 1 can maintain its single‐crystal structure even kept in air at 400 °C for 3 h, and in DMF or water at 200 °C for 7 days. Density functional theory (DFT) calculations suggested that the high interaction energy between the [Th 6 O 4 (OH) 4 (H 2 O) 6 ] 12+ clusters and ligands was responsible for the excellent stability of 1 . Catalytic investigations revealed that 1 can effectively and size‐selectively catalyze the reductive amination of aldehydes with DMF, and it can be reused at least five times without obvious loss in catalytic activity.

Topics & Concepts

Reductive aminationChemistryCluster (spacecraft)DimethylformamideCombinatorial chemistryAminationCatalysisOrganic chemistryComputer scienceOperating systemSolventAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisOrganoboron and organosilicon chemistry
A Strong‐Acid‐Resistant [Th<sub>6</sub>] Cluster‐Based Framework for Effectively and Size‐Selectively Catalyzing Reductive Amination of Aldehydes with <i>N</i>,<i>N</i>‐Dimethylformamide | Litcius