Alkaloid-induced asymmetric hydrogenation on bimetallic Pt@Cu cathodes under electrochemical conditions

Yue, Ying-Na; Wu, Di; Zeng, Sheng; Yang, Man-Ping; Wang, Huan; Lu, Jia‐Xing

doi:10.1039/c7nj00844a

Cited by 17 publications

(10 citation statements)

References 24 publications

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“…Finally, alloying Pt with earth-abundant transition metals, like Cu, to form bimetallic nanoparticles has received considerable attention because such species have shown activity in proton-exchange membrane full cells and electrocatalysis, such as CO 2 reduction. The use of core–shell Pt@Cu particles with Cu as core and Pt as shell not only reduces the cost of using Pt but also shows superior catalytic activity compared to using pure Pt. − Therefore, we also study the stability of Pt clusters on TBAPy linkers and we compare our findings to those for Cu clusters.…”

Section: Introductionmentioning

confidence: 99%

Organic Linker Effect on the Growth and Diffusion of Cu Clusters in a Metal–Organic Framework

Cramer

Truhlar

2018

J. Phys. Chem. C

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One reason that metal nanoparticles encapsulated in metal−organic frameworks are of interest is that confinement effects on the particle size and shape may lead to superior catalytic activity. The interior of a metal–organic framework has the potential to influence nucleation and aggregation of metal nanoparticles and to strongly affect their in situ shape and electronic properties. We apply density functional theory and ab initio molecular dynamics (AIMD) to model the nucleation and diffusion of Cu n (n = 1–19) clusters on the tetratopic 1,3,6,8-(p-benzoate)pyrene (TBAPy4–) linkers of NU-1000 frameworks. We find that Cu atoms and Cu clusters are stabilized by the TBAPy linker, especially by the edge site of aromatic rings. The stabilization increases when the Cu cluster interacts with two linkers. We identified the most favorable site for Cu cluster adsorption as the window site that connects the c pore and the triangular pore. A Pt atom is found to bind much more strongly than a Cu atom on the TBAPy linker, and AIMD simulations show that this promotes Pt atom diffusion from the center of a Cu15 cluster to the interface between the linker and the cluster. The strong interaction between a Pt atom and a linker is attributed to the greater metal-to-linker charge transfer.

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Section: Introductionmentioning

confidence: 99%

Organic Linker Effect on the Growth and Diffusion of Cu Clusters in a Metal–Organic Framework

Cramer

Truhlar

2018

J. Phys. Chem. C

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“…The low enantioselectivity of this system was attributed to poor distribution of the chiral tartaric acid across the electrode. Subsequent methods used chiral polymer-coated (such as a poly- l -valine graphite cathode), transition-metal-complexed − (Rh and Pd), or alkaloid-doped − (yohimbine, strychnine, and cinchonidine) electrodes for the AH of olefins and carbonyl derivatives with low to moderate stereoselectivities. Enzyme-catalyzed electrochemical reductions have also been reported.…”

Section: Future Prospectsmentioning

confidence: 99%

Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis

2021

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Tandem catalysis enables the rapid construction of complex architectures from simple building blocks. This Perspective shares our interest in combining stereoselective hydrogenation with transformations such as isomerization, oxidation, and epimerization to solve diverse challenges. We highlight the use of tandem hydrogenation for preparing complex natural products from simple prochiral building blocks and present tandem catalysis involving transfer hydrogenation and dynamic kinetic resolution. Finally, we underline recent breakthroughs and opportunities for asymmetric hydrogenation.

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“…Further, alkaloid-induced asymmetric electrochemical hydrogenation of 2,2,2-trifluoroacetophenone 32 nanoparticles was also developed (Scheme 13). These NPs with low Pt loading were further obtained by reducing platinum precursors on Cu NPs [41].…”

Section: Reviewmentioning

confidence: 99%

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

Ghosh

Shinde

Rueping

2019

Beilstein J. Org. Chem.

163

101

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The direct exploitation of ‘electrons’ as reagents in synthetic organic transformations is on the verge of a renaissance by virtue of its greenness, sustainability, atom economy, step economy and inherent safety. Achieving stereocontrol in such organic electrochemical reactions remains a major synthetic challenge and hence demands great expertise. This review provides a comprehensive discussion of the details of stereoselective organic electrochemical reactions along with the synthetic accomplishments achieved with these methods.

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Alkaloid-induced asymmetric hydrogenation on bimetallic Pt@Cu cathodes under electrochemical conditions

Abstract: Pt@Cu NPs were coated on carbon paper and used as a cathode for asymmetric electrohydrogenation of pro-chiral aromatic ketones catalyzed by cinchonidine (CD) alkaloids.

Cited by 17 publications

References 24 publications

Organic Linker Effect on the Growth and Diffusion of Cu Clusters in a Metal–Organic Framework

Organic Linker Effect on the Growth and Diffusion of Cu Clusters in a Metal–Organic Framework

Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

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