Synthesis of nitriles by the electro-oxidative coupling of primary alcohols and ammonia on Pd nanoparticle-modified CuO nanowires in oxidant-free electrolytes under ambient conditions

Fang, Zhiyong; Ding, Yunxuan; Wang, Mei; Wang, Linqin; Li, Fusheng; Fan, Ke; Wu, Xiujuan; Sun, Licheng; Zhang, Peili

doi:10.1016/j.apcatb.2023.122999

Cited by 12 publications

(3 citation statements)

References 57 publications

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“…This facilitates oxidation–reduction reactions to take place under mild reaction conditions. 64 Therefore, electrocatalysis provides a significant advancement in the development of electrocatalytic systems for oxidative cyanation reactions.…”

Section: Discussionmentioning

confidence: 99%

Thermo-/photo-catalysts for aerobic oxidative cyanation of diverse oxygen-containing feedstocks

He,

Zhou,

Zhang

et al. 2024

Green Chem.

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Section: Discussionmentioning

confidence: 99%

Thermo-/photo-catalysts for aerobic oxidative cyanation of diverse oxygen-containing feedstocks

He,

Zhou,

Zhang

et al. 2024

Green Chem.

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“…[38,39] Moreover, Zhang and co-workers have developed an efficient electro-oxidative coupling strategy for the synthesis of various nitriles with moderate to high yields from corresponding alcohols and aqueous ammonia under mild conditions. [40] Their bimetallic electrocatalyst consists of Cu and a noble metal Pd, which acted as the sites for the oxidation and coupling reactions, respectively. Therefore, opportunities exist for electrocatalytic nitrile synthesis from alcohols.…”

Section: Introductionmentioning

confidence: 99%

Electrosynthesis of nitriles from primary alcohols and ammonia on Ni catalyst

Xiao,

Lim,

Gao

et al. 2024

Preprint

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Despite the increasing interest on electrocatalytic refinery of renewable feedstocks to produce value-added chemicals, nitrile electrosynthesis from alcohols is rarely studied. Here, we report the direct electrosynthesis of nitriles from primary alcohols and ammonia, with a simple nickel catalyst under benign conditions in aqueous electrolytes. The highest benzonitrile faradaic efficiency of 63.0% was achieved at 1.375 V vs. RHE. The reaction proceeds via a dehydrogenation-imination-dehydrogenation sequence, with the rate-determining step likely involving the cleavage of α-carbon C-H bond of the alcohol. Based on the electrochemical and in-situ Raman analyses, we propose that the in-situ formed Ni2+/Ni3+ redox species serves as the active site for converting alcohol to nitrile, while Ni2+ also exhibits capability for the oxidation of imine. Various aromatic, aliphatic and heterocyclic primary alcohols were transformed to the corresponding nitriles, exhibiting broad feasibility. This study offers a promising electrocatalytic system for the sustainable synthesis of high-value nitriles.

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“…Pd@CuO, used as an anodic electrode, resulted in the electro-oxidative coupling of benzyl alcohol and ammonia, producing 83.2% of benzonitrile. Tis method was also successful in converting various primary alcohols to nitriles [16]. Xiao et al [17] developed an efcient chemoenzymatic strategy to prepare nitriles from benzylamine by combining selective oxidation and dehydration.…”

Section: Introductionmentioning

confidence: 99%

Unlocking the Potential of NiSO4·6H2O/NaOCl/NaOH Catalytic System: Insights into Nickel Peroxide as an Intermediate for Benzonitrile Synthesis in Water

Shoair,

Almalki,

Shanab

et al. 2023

Journal of Nanotechnology

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Nickel peroxide nanoparticles (NPNPs) were prepared and characterized using various techniques including transmission electron microscope (TEM), scan electron microscope (SEM), energy dispersive spectrometer (EDS), X-ray diffraction (XRD), and FTIR spectra. The aqueous basic catalytic system NiSO4·6H2O/NaOCl/NaOH (pH = 14) was investigated for the catalytic dehydrogenation of benzylamine and parasubstituents to their corresponding nitriles at room temperature. The obtained results confirmed the formation of NiO2 nanocrystalline particles with a size of 20 nm. Benzylamine with electron-donating groups showed higher yields of nitriles compared to electron-withdrawing groups. The mechanism involved in the in situ generated NiO2 nanoparticles dehydrogenating benzylamine to benzonitrile, with the produced NiO converting back to NiO2 nanoparticles through the excess of NaOCl.

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Synthesis of nitriles by the electro-oxidative coupling of primary alcohols and ammonia on Pd nanoparticle-modified CuO nanowires in oxidant-free electrolytes under ambient conditions

Cited by 12 publications

References 57 publications

Thermo-/photo-catalysts for aerobic oxidative cyanation of diverse oxygen-containing feedstocks

Thermo-/photo-catalysts for aerobic oxidative cyanation of diverse oxygen-containing feedstocks

Electrosynthesis of nitriles from primary alcohols and ammonia on Ni catalyst

Unlocking the Potential of NiSO4·6H2O/NaOCl/NaOH Catalytic System: Insights into Nickel Peroxide as an Intermediate for Benzonitrile Synthesis in Water

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