Chiral Macrocycle‐Enabled Counteranion Trapping for Boosting Highly Efficient and Enantioselective Catalysis

Rui, Ning; Zhou, Hao; Nie, Suping; Ao, Yu‐Fei; Wang, De‐Xian; Wang, Qi‐Qiang

doi:10.1002/ange.202003673

Cited by 12 publications

(2 citation statements)

References 60 publications

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“…Besides, Wang’s group developed a counteranion trapping strategy with macrocyclic compounds for enantioselective catalysis. The macrocycles contained cooperative moieties to construct a chiral catalytic cavity ( Ning et al, 2020 ). Their catalytic microenvironment was further optimized with functionalization for the regulation of substrate-binding.…”

Section: Single-molecule Macrocycles As Bioinspired Catalystsmentioning

confidence: 99%

Macrocycles in Bioinspired Catalysis: From Molecules to Materials

2021

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Macrocyclic compounds have been studied extensively as the host molecules in supramolecular chemistry. Their structural characteristics make macrocycles desirable in the field of molecular recognition, which is the key to high catalytic efficiencies of natural enzymes. Therefore, macrocycles are ideal building blocks for the design of bioinspired catalysts. This mini review highlights recent advances ranging from single-molecule to metal-organic framework materials, exhibiting multilevel macrocycle catalysts with unique catalytic centers and substrate-binding affinities.

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Section: Single-molecule Macrocycles As Bioinspired Catalystsmentioning

confidence: 99%

Macrocycles in Bioinspired Catalysis: From Molecules to Materials

2021

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“…Novel and functional macrocyclic hosts with conformational change and cavity tunability have sparked a lot of interest in molecular recognition and supramolecular materials. − They also serve as promising building blocks in the design of coordination supramolecular architectures with rich host–guest chemistry. − Recently, we have reported a flexible organopalladium host built from a dynamic macrocyclic ligand with two m -methylphenyl linkers, which exhibited both induced-fit guest binding and efficient photooxidation catalysis.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Interconversion and Induced-Fit Guest Binding with Two Macrocycle-Based Coordination Cages

Xia

Zhong

et al. 2023

Inorg. Chem.

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We report the syntheses and host–guest chemistry of two interconvertible coordination cages, Pd2L2 and Pd1L1, from a dynamic macrocycle ligand (L) and a cis-blocking (tmen)Pd(NO3)2 (tmen = tetramethylethylenediamine) unit (Pd). The water-soluble macrocyclic L, which can bind various polycyclic aromatic hydrocarbon (PAH) guests in its cis-conformation, was constructed via four pyridinium bonds between two 2,4,6-tri(4-pyridyl)-1,3,5-triazine [TPT] panels and two p-xylene bridges. We selectively formed each cage either by changing the reaction concentration/solvent/temperature or through induced-fit guest encapsulation, while direct assembly of L and Pd resulted in a mixture of Pd2L2 and Pd1L1 in equilibrium. X-ray structures of the free ligand and the host–guest complexes confirmed the induce-fit adaptive changes in the ligand’s conformation and the cage’s cavity. This work demonstrates a useful strategy for designing multistimuli-responsive supramolecular hosts by coordination self-assembly with macrocyclic ligands featuring rich conformational freedom.

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N,N‐Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion‐Binding Catalysis

et al. 2021

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An enantioselective anion-binding organocatalytic approach with versatile N,N-dialkylhydrazones (DAHs) as polarity-reversed (umpolung) nucleophiles is presented. For the application of this concept, a highly ordered hydrogenbond (HB) network between a carefully selected CF 3-substituted triazole-based multidentate HB-donor catalyst, the ionic substrate and the hydrazone in a supramolecular chiral ionpair complex was envisioned. The formation of such a network was further supported by both experimental and computational studies, which showed the crucial role of the anion as a template unit. The asymmetric Reissert-type reaction of quinolines as a model test reaction chemoselectively delivered highly enantiomerically enriched hydrazones (up 95:5 e.r.) that could be further derivatized to value-added compounds with up to three stereocenters.

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Chiral Macrocycle‐Enabled Counteranion Trapping for Boosting Highly Efficient and Enantioselective Catalysis

Cited by 12 publications

References 60 publications

Macrocycles in Bioinspired Catalysis: From Molecules to Materials

Macrocycles in Bioinspired Catalysis: From Molecules to Materials

Dynamic Interconversion and Induced-Fit Guest Binding with Two Macrocycle-Based Coordination Cages

N,N‐Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion‐Binding Catalysis

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