Supramolecule-Controlled Enantioselectivity for Electrochemical Asymmetric Hydrogenation of Coumarins with a Chiral Macrocyclic Compound

Xue, Yan-Fang; Liu, Jie; Ge, Qingmei; Jiang, Nan; Zhao, Wenfeng; Liu, Mao; Cong, Hang; Zhao, Jiang‐Lin

doi:10.1021/acs.orglett.3c00653

Cited by 3 publications

(2 citation statements)

References 34 publications

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“…the supramolecular strategy encoded chiral macrocyclic multifarane[3,3] displayed asymmetric hydrogenation of 4‐methylumbelliferone in electrochemical reduction and produced L‐7‐hydroxy‐4‐methylchroman2‐one product with a yield of 65% and enantioselectivity up to >99%, which also exhibited high stability and repeatability. [ 250 ] Based on reversible addition‐fragmentation chain transfer polymerization, the water‐soluble single‐chain polymeric NPs consisting of CO 2 ‐switchable copolymers were synthesized by copolymerization of amidine derivatives with hydrophobic chiral salen Fe III monomers that displayed asymmetric sulfa‐Michael addition. [ 254 ] The stereoselectivity of the chiral supramolecular catalyst is greatly improved when encased in a supramolecular non‐chiral cage during converts styrene derivatives into aldehyde products with much higher chiral induction than the nonencapsulated catalyst with selectivity of 71 ± 3% ee.…”

Section: Selective Catalysis Activity Of Chiral Nanomaterialsmentioning

confidence: 99%

“…The supramolecular chiral assemblies were also important as biomimetic nanozymes in which chirality could originate from integrated chiral molecules or assembled chiral geometries. [ 249 , 250 , 251 ] Based on the polymer supramolecular chirality to enhance catalytic efficiency, control over enantioselectivity was gaining increasing interest. [ 252 ] The assembled supramolecular chiral nanostructures were demonstrated as nanocages, nanotubes, nanorods, micelles, vesicles, and so on with asymmetric catalysis activity.…”

Section: Selective Catalysis Activity Of Chiral Nanomaterialsmentioning

confidence: 99%

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Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Cao,

Yang,

Kim

et al. 2024

Advanced Science

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Chiral nanomaterials with unique chiral configurations and biocompatible ligands have been booming over the past decade for their interesting chiroptical effect, unique catalytical activity, and related bioapplications. The catalytic activity and selectivity of chiral nanomaterials have emerged as important topics, that can be potentially controlled and optimized by the rational biochemical design of nanomaterials. In this review, chiral nanomaterials synthesis, composition, and catalytic performances of different biohybrid chiral nanomaterials are discussed. The construction of chiral nanomaterials with multiscale chiral geometries along with the underlying principles for enhancing chiroptical responses are highlighted. Various biochemical approaches to regulate the selectivity and catalytic activity of chiral nanomaterials for biocatalysis are also summarized. Furthermore, attention is paid to specific chiral ligands, materials compositions, structure characteristics, and so on for introducing selective catalytic activities of representative chiral nanomaterials, with emphasis on substrates including small molecules, biological macromolecule, and in‐site catalysis in living systems. Promising progress has also been emphasized in chiral nanomaterials featuring structural versatility and improved chiral responses that gave rise to unprecedented chances to utilize light for biocatalytic applications. In summary, the challenges, future trends, and prospects associated with chiral nanomaterials for catalysis are comprehensively proposed.

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Section: Selective Catalysis Activity Of Chiral Nanomaterialsmentioning

confidence: 99%

Section: Selective Catalysis Activity Of Chiral Nanomaterialsmentioning

confidence: 99%

Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Cao,

Yang,

Kim

et al. 2024

Advanced Science

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Atomically Dispersed Gold Nanoclusters and Single Atoms Coexisting Chiral Electrode for High‐Performance Enantioselective Electrosynthesis using H₂o as Hydrogen Source

Chang,

Qi,

Wang

et al. 2024

Adv Funct Materials

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Developing chiral electrode catalysts for enantioselective electrosynthesis is a great challenge, as it requires catalysts that possess both high activity and enantioselectivity. Precise synthesis of nanoclusters and single atoms coexisting chiral catalysts provide a promising pathway for enhancing asymmetric catalytic performance. Herein, chiral electrode catalysts are fabricated comprising gold clusters (R‐AuC) and single atoms (R‐AuS) on graphene oxide (R‐AuC/S@GO) through an assembly‐irradiation strategy. Thereinto, the R‐Aus is in situ generated from R‐AuC under light irradiation. The monoatomization process can be precisely regulated by changing the wavelength of the light, resulting in four Au‐based chiral electrode (R‐Au@GO) catalysts with different ratios of nanoclusters and single atoms. These chiral electrodes are applied in the electrocatalytic enantioselective hydrogenation of methyl benzoylformate (MB) to chiral methyl mandelate (S‐MM), and the R‐AuC/S‐2@GO with ≈26% R‐AuC and 74% R‐AuS achieve the highest catalytic activity (35 µmol cm−2 h−1 productivity) and enantioselectivity [97% enantiomeric excess (ee)]. Detailed experimental analysis and density functional theory calculations reveal that the R‐AuS on GO promotes the in situ generation of H* species, and R‐AuC mainly drives the enantioselective conversion of MB by transferring the H* species to the carbonyl group of MB, ultimately yielding chiral S‐MM.

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Asymmetric electrosynthesis: emerging catalytic strategies and mechanistic insights

Jiang,

Zou,

Zhuang

et al. 2025

Green Chem.

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Supramolecule-Controlled Enantioselectivity for Electrochemical Asymmetric Hydrogenation of Coumarins with a Chiral Macrocyclic Compound

Cited by 3 publications

References 34 publications

Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Atomically Dispersed Gold Nanoclusters and Single Atoms Coexisting Chiral Electrode for High‐Performance Enantioselective Electrosynthesis using H₂o as Hydrogen Source

Asymmetric electrosynthesis: emerging catalytic strategies and mechanistic insights

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Supramolecule-Controlled Enantioselectivity for Electrochemical Asymmetric Hydrogenation of Coumarins with a Chiral Macrocyclic Compound

Cited by 3 publications

References 34 publications

Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Biomimetic Chiral Nanomaterials with Selective Catalysis Activity

Atomically Dispersed Gold Nanoclusters and Single Atoms Coexisting Chiral Electrode for High‐Performance Enantioselective Electrosynthesis using H2o as Hydrogen Source

Asymmetric electrosynthesis: emerging catalytic strategies and mechanistic insights

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Product

Resources

About

Atomically Dispersed Gold Nanoclusters and Single Atoms Coexisting Chiral Electrode for High‐Performance Enantioselective Electrosynthesis using H₂o as Hydrogen Source