Alcohol imination catalyzed by carbon nanostructures synthesized by C(sp2)-C(sp3) free radical coupling

Wang, Cheng; Qiao, Zirui; Tian, Yan; Yang, Haijun; Cao, Huaqiang; Cheetham, Anthony K.

doi:10.1016/j.isci.2023.106659

iScience

2023

DOI: 10.1016/j.isci.2023.106659

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Alcohol imination catalyzed by carbon nanostructures synthesized by C(sp2)-C(sp3) free radical coupling

Cheng Wang¹,

Zirui Qiao²,

Yan Tian³

et al.

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2024

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Cited by 3 publications

References 57 publications

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Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Qiao,

Cao,

Wang

et al. 2024

Angewandte Chemie

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Here, we report curvature‐induced electron spin catalysis by using solid carbon spheres as catalysts, which were synthesized using positive curvature molecular hexabromocyclopentadiene as a precursor molecule, following a radical coupling mechanism. The curvature spin of carbon is regarded as an overlapping state of σ‐ and π‐radical, which is identified by the inverse Laplace transform of pulse‐electron paramagnetic resonance. The growth mechanism of carbon spheres abiding by Kroto's model, is supported by the density functional theory study of thermodynamics and kinetics calculations. The solid carbon spheres present excellent catalytic behaviour of oxidation coupling of amines to form corresponding imines with the conversion of >99 %, selectivity of 98.7 %, and yield of 97.7 %, which is attributed to the predominantly curvature‐induced electron spin catalysis of carbon, supported by the calculation of oxygen adsorption energy. This work proposes a view of curvature‐induced spin catalysis of carbon, which opens up a research direction for curvature‐induced electron spin catalysis.

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Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Qiao,

Cao,

Wang

et al. 2024

Angewandte Chemie

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Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Qiao,

Cao,

Wang

et al. 2024

Angew Chem Int Ed

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Photocatalytic Oxidative Coupling of Benzyl Alcohol and Benzylamine for Imine Synthesis Using Immobilized Cs₃Bi₂Br₉ Perovskite

Lopes,

Peñas‐Garzón,

Sampaio

et al. 2024

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The oxidative cross‐coupling of benzyl alcohol (BA) and benzylamine (BZA) is employed for the production of the corresponding imine, N‐benzylidenebenzylamine (BZI), under visible light irradiation (light‐emitting diodes (LE with λmax = 417 nm) and mild reaction conditions. The cesium bismuth halide perovskites (Cs2Bi3Br9, CBB) are synthesized by a one‐step solution process as a sustainable alternative for the widely used Pb‐halide perovskites. The CBB photocatalyst is immobilized on a polyethylene terephthalate (PET) structure designed explicitly for three‐dimensional (3D) printing to operate in both batch and continuous modes to overcome the need for a final catalyst separation step. The complete conversion of BZA and BA is achieved after 1 h, yielding 70% of BZI in basic medium operating in batch mode. Comparable results are found between the suspended and immobilized catalysts for imine production. Additionally, continuous production of BZI is successfully achieved using immobilized CBB, with a maximum yield of 0.35 mm of BZI after a 2 h reaction. The supported CBB perovskites demonstrate high stability after multiple uses. Finally, a comprehensive photocatalytic pathway for cross‐coupling BZA with BA is proposed.

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Alcohol imination catalyzed by carbon nanostructures synthesized by C(sp2)-C(sp3) free radical coupling

Cited by 3 publications

References 57 publications

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Photocatalytic Oxidative Coupling of Benzyl Alcohol and Benzylamine for Imine Synthesis Using Immobilized Cs₃Bi₂Br₉ Perovskite

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Alcohol imination catalyzed by carbon nanostructures synthesized by C(sp2)-C(sp3) free radical coupling

Cited by 3 publications

References 57 publications

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Curvature‐Induced Electron Spin Catalysis with Carbon Spheres

Photocatalytic Oxidative Coupling of Benzyl Alcohol and Benzylamine for Imine Synthesis Using Immobilized Cs3Bi2Br9 Perovskite

Contact Info

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Photocatalytic Oxidative Coupling of Benzyl Alcohol and Benzylamine for Imine Synthesis Using Immobilized Cs₃Bi₂Br₉ Perovskite