Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers

Zhang, Xin; Wang, Fucheng; Tan, Choon Hong

doi:10.1021/jacsau.2c00626

Cited by 59 publications

(53 citation statements)

References 96 publications

(118 reference statements)

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“…43 The signal intensities of Pd@ SiO 2 /ZSM-5-20 are stronger and broader than Pd/ZSM-5 at R = ∼1.0−2.0 Å, as seen from the wavelet transform plot (Figure 2c,e), due to the coexistence of Pd−O and Pd−Si bonds. The formation of Pd−Si bonds is most likely the result of a mechanism proposed by Duprez et al 44 in which hydrogen spillover from metal to oxide reduces silica to Si 0 , which further migrates to the near surface of Pd NPs 45,46 as follows:…”

Section: Synthesis and Physicochemical Propertiesmentioning

confidence: 99%

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Dong

et al. 2023

JACS Au

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Engineering the interfacial structure between noble metals and oxides, particularly on the surface of non-reducible oxides, is a challenging yet promising approach to enhancing the performance of heterogeneous catalysts. The interface site can alter the electronic and d-band structure of the metal sites, facilitating the transition of energy levels between the reacting molecules and promoting the reaction to proceed in a favorable direction. Herein, we created an active Pd–Si interface with tunable electronic metal–support interaction (EMSI) by growing a thin permeable silica layer on a non-reducible oxide ZSM-5 surface (termed Pd@SiO2/ZSM-5). Our experimental results, combined with density functional theory calculations, revealed that the Pd–Si active interface enhanced the charge transfer from deposited Si to Pd, generating an electron-enriched Pd surface, which significantly lowered the activation barriers for O2 and H2O. The resulting reactive oxygen species, including O2 –, O2 2–, and −OH, synergistically facilitated formaldehyde oxidation. Additionally, moderate electronic metal–support interaction can promote the catalytic cycle of Pd0 ⇆ Pd2+, which is favorable for the adsorption and activation of reactants. This study provides a promising strategy for the design of high-performance noble metal catalysts for practical applications.

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Section: Synthesis and Physicochemical Propertiesmentioning

confidence: 99%

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Dong

et al. 2023

JACS Au

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“…Zhang and co-workers show that by altering the surface composition of Cu species using just electrodeposition voltages, the selectivity of CO 2 RR on Cu GDEs may be switched between C 2+ products (mostly C 2 H 4 ) and CH 4 . 95 A novel Co phthalocyanine (CoPc 2 ) with a trimethylammonium moiety and three tertbutyl groups attached to the phthalocyanine macrocycle is created by Wang and his colleagues. 96 In order to achieve CO 2 to CO conversion in an industrial environment, CoPc 2 was integrated by assembling GDEA-cells that contained CoPc 2 supported on a GDE as the cathode.…”

Section: Conventional Flow Cellsmentioning

confidence: 99%

Bridging Trans-Scale Electrode Engineering for Mass CO₂ Electrolysis

Wen

Ren

Liu

et al. 2023

JACS Au

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Electrochemical CO 2 upgrade offers an artificial route for carbon recycling and neutralization, while its widespread implementation relies heavily on the simultaneous enhancement of mass transfer and reaction kinetics to achieve industrial conversion rates. Nevertheless, such a multiscale challenge calls for trans-scale electrode engineering. Herein, three scales are highlighted to disclose the key factors of CO 2 electrolysis, including triple-phase boundaries, reaction microenvironment, and catalytic surface coordination. Furthermore, the advanced types of electrolyzers with various electrode design strategies are surveyed and compared to guide the system architectures for continuous conversion. We further offer an outlook on challenges and opportunities for the grand-scale application of CO 2 electrolysis. Hence, this comprehensive Perspective bridges the gaps between electrode research and CO 2 electrolysis practices. It contributes to facilitating the mixed reaction and mass transfer process, ultimately enabling the on-site recycling of CO 2 emissions from industrial plants and achieving net negative emissions.

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“…S–N containing compounds are also able to form diverse chiral structures due to their multiple oxidation states, including many S(IV) and S(VI) stereogenic centers, which are usually neglected by drug discovery programs. These stereogenic centers are underexplored as pharmacophores even though they can significantly increase the structural diversity and complexity of drug candidates . Given the potential chemistry available via S–N bonds, e.g., reversible formation and functionalization, coupled with the biological and pharmaceutical current and potential uses of cyclic peptides, ,, there is a need to understand the factors that may be important for the formation of cyclic peptides via such bonds .…”

Section: Introductionmentioning

confidence: 99%

Computational Insights into the Formation and Structure of S–N Containing Cyclic Peptides

2023

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Cyclic peptides are known to have biologically important roles and may also be applicable to the pharmaceutical and other industries. Furthermore, thiols and amines, which are found throughout biological systems, can react to form S−N bonds and to date, ∼100 biomolecules containing such a bond have been identified. However, while there are in principle numerous S−N containing peptide-derived rings possible, only a few are presently known to occur in biochemical systems. Density functional theorybased calculations have been used to consider the formation and structure of S−N containing cyclic peptides from systematic series of linear peptides in which a cysteinyl has first been oxidized to a sulfenic or sulfonic acid. In addition, the possible effect of the cysteine's vicinal residue on the free energy of formation has also been considered. In general, when the cysteine is first oxidized to a sulfenic acid, only the formation of smaller S−N containing rings is calculated to be exergonic in aqueous solution. In contrast, when the cysteine is first oxidized to a sulfonic acid, the formation of all rings considered (with one exception) is calculated to be endergonic in aqueous solution. The nature of vicinal residue can influence ring formation through stabilizing or destabilizing intramolecular interactions.

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Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers

Cited by 59 publications

References 96 publications

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Bridging Trans-Scale Electrode Engineering for Mass CO₂ Electrolysis

Computational Insights into the Formation and Structure of S–N Containing Cyclic Peptides

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Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers

Cited by 59 publications

References 96 publications

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O2 and H2O Activation

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O2 and H2O Activation

Bridging Trans-Scale Electrode Engineering for Mass CO2 Electrolysis

Computational Insights into the Formation and Structure of S–N Containing Cyclic Peptides

Contact Info

Product

Resources

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Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Tunable Interfacial Electronic Pd–Si Interaction Boosts Catalysis via Accelerating O₂ and H₂O Activation

Bridging Trans-Scale Electrode Engineering for Mass CO₂ Electrolysis