1,2-Amino oxygenation of alkenes with hydrogen evolution reaction

Liu, Shengzhang; Wang, Shengchun; Wang, Pengjie; Huang, Zhiliang; Wang, Tao; Lei, Aiwen

doi:10.1038/s41467-022-32084-8

Cited by 27 publications

(9 citation statements)

References 44 publications

(49 reference statements)

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“…The adsorbate on PdO via μ-CCHCH 3 configuration, where anomeric carbon of the vinyl group adsorbs on PdO via the bridge bonds on adjacent Pd and O atoms, leads to the generation of propene glycol. Consequently, the high content of oxygen on metal oxide results in a 3 times higher turnover frequency (TOF) on PdO/C than on metal Pd/C for producing propene glycol, which is one of the highly valuable chemicals pursued from propene conversion. − This work expands a new understanding of propene electrooxidation compared to thermocatalytic oxidation.…”

Section: Introductionmentioning

confidence: 99%

Reaction Mechanism and Selectivity Tuning of Propene Oxidation at the Electrochemical Interface

et al. 2022

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Electrochemical conversion of propene is a promising technique for manufacturing commodity chemicals by using renewable electricity. To achieve this goal, we still need to develop high-performance electrocatalysts for propene electrooxidation, which highly relies on understanding the reaction mechanism at the molecular level. Although the propene oxidation mechanism has been well investigated at the solid/gas interface under thermocatalytic conditions, it still remains elusive at the solid/liquid interface under an electrochemical environment. Here, we report the mechanistic studies of propene electrooxidation on PdO/C and Pd/C catalysts, considering that the Pd-based catalyst is one of the most promising electrocatalytic systems. By electrochemical in situ attenuated total reflection Fourier transform infrared spectroscopy, a distinct reaction pathway was observed compared with conventional thermocatalysis, emphasizing that propene can be dehydrogenated at a potential higher than 0.80 V, and strongly adsorb via μ-CCHCH3 and μ3-η2-CCHCH3 configuration on PdO and Pd, respectively. The μ-CCHCH3 is via bridge bonds on adjacent Pd and O atoms on PdO, and it can be further oxidized by directly taking surface oxygen from PdO, verified by the H2 18O isotope-edited experiment. A high surface oxygen content on PdO/C results in a 3 times higher turnover frequency than that on Pd/C for converting propene into propene glycol. This finding highlights the different reaction pathways under an electrochemical environment, which sheds light on designing next-generation electrocatalysts for propene electrooxidation.

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Section: Introductionmentioning

confidence: 99%

Reaction Mechanism and Selectivity Tuning of Propene Oxidation at the Electrochemical Interface

et al. 2022

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“…Due to the wide chemical diversity of clinically used 1,2amino alcohols, most notably in β-adrenergic receptor agonists (β-blockers, Figure 1b), [18][19][20] there is continued motivation to expand routes to this class of compounds. [21,22] Further, their relative simplicity serves as a fertile testing ground for promiscuous biocatalytic synthesis. Sehl et al described a cascade that produced norephedrine stereoisomers in high yields from benzaldehyde using a lyase and transaminase.…”

Section: Introductionmentioning

confidence: 99%

Engineering Enzyme Substrate Scope Complementarity for Promiscuous Cascade Synthesis of 1,2‐Amino Alcohols

et al. 2022

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Biocatalytic cascades are uniquely powerful for the efficient, asymmetric synthesis of bioactive compounds. However, high substrate specificity can hinder the scope of biocatalytic cascades because the constituent enzymes may have non‐complementary activity. In this study, we implemented a substrate multiplexed screening (SUMS) based directed evolution approach to improve the substrate scope overlap between a transaldolase (ObiH) and a decarboxylase for the production of chiral 1,2‐amino alcohols. To generate a promiscuous cascade, we engineered a tryptophan decarboxylase to act efficiently on β‐OH amino acids while avoiding activity on l‐threonine, which is needed for ObiH activity. We leveraged this exquisite selectivity with matched substrate scope to produce a variety of enantiopure 1,2‐amino alcohols in a one‐pot cascade from aldehydes or styrene oxides. This demonstration shows how SUMS can be used to guide the development of promiscuous, C−C bond forming cascades.

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“…High pressure can provide a good way to search for new materials with new crystal phases, nonconventional stoichiometry, and outstanding properties. [1][2][3][4][5] For instance, unexpected stable stoichiometry of some binary systems were predicted under pressure. 6,7 Furthermore, the pressure-induced electronic topological transition in the structure of IrP has been uncovered by Ma by rst-principles calculations.…”

Section: Introductionmentioning

confidence: 99%

Phase transition and electronic properties of Co–As binary compounds at high pressure

et al. 2022

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1,2-Amino oxygenation of alkenes with hydrogen evolution reaction

Cited by 27 publications

References 44 publications

Reaction Mechanism and Selectivity Tuning of Propene Oxidation at the Electrochemical Interface

Reaction Mechanism and Selectivity Tuning of Propene Oxidation at the Electrochemical Interface

Engineering Enzyme Substrate Scope Complementarity for Promiscuous Cascade Synthesis of 1,2‐Amino Alcohols

Phase transition and electronic properties of Co–As binary compounds at high pressure

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