Sunlight assisted synthesis of α-aminonitrile using Capillary flow microreactor: A new approach

Yunus, Ismaila Abdulkareem; Basheer, Chanbasha; Al‐Muallem, Hasan A.

doi:10.1016/j.jece.2016.05.025

Cited by 8 publications

(1 citation statement)

References 13 publications

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“…, in the syntheses of natural products, peptide bond formation, as building blocks for various heterocycles or for general α-functionalization of amines in cross-dehydrogenative coupling reactions − ). During the past decades, plenty of (photocatalyzed) approaches toward α-aminonitriles have been reported, ,− but to the best of our knowledge, only very few of them make direct use of near-infrared light as the energy source, and they mainly focus on triplet fusion upconversion or suffer from time-consuming catalyst preparation. , Parallel to our work, the Furuyama group very recently reported the application of different sulfur-substituted zinc phthalocyanine catalysts in the context of various NIR-driven CDC reactions in methanol/pyridine mixtures . Herein, we report a protocol using unsubstituted zinc phthalocyanine (ZnPc) as an inexpensive commercial photosensitizer in acetonitrile as an environmentally benign solvent, − for the efficient and scalable near-infrared photocatalyzed formation of α-aminonitriles.…”

Section: Introductionmentioning

confidence: 74%

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

et al. 2022

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While photochemical transformations with sunlight almost exclusively utilize the UV–vis part of the solar spectrum, the majority of the photons emitted by the sun have frequencies in the near-infrared region. Phthalocyanines show high structural similarity to the naturally occurring light-harvesting porphyrins, chlorins, and mainly bacteriochlorins and are also known for being efficient and affordable near-infrared light absorbers as well as triplet sensitizers for the production of singlet oxygen. Although having been neglected for a long time in synthetic organic chemistry due to their low solubility and high tendency toward aggregation, their unique photophysical properties and chemical robustness make phthalocyanines attractive photocatalysts for the application in near-infrared-light-driven synthesis strategies. Herein, we report a cheap, simple, and efficient photocatalytic protocol, which is easily scalable under continuous-flow conditions. Various phthalocyanines were studied as near-infrared photosensitizers in oxidative cyanations of tertiary amines to generate α-aminonitriles, a synthetically versatile compound class.

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Section: Introductionmentioning

confidence: 74%

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

et al. 2022

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Visible‐Light‐Driven Enantioselective Aerobic Oxidation of β‐Dicarbonyl Compounds Catalyzed by Cinchona‐Derived Phase Transfer Catalysts in Batch and Semi‐Flow

Tang

Zhao

et al. 2019

Adv Synth Catal

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The direct asymmetric α‐hydroxylation of β‐dicarbonyl compounds has been developed using cinchona‐derived phase‐transfer catalysts in batch and semi‐flow processes. Using visible light as the driving force and air as oxidant, the corresponding products were obtained in excellent yields (up to 96%) and good enantioselectivities (up to 90% ee). The catalyst acts as a chiral center and a catalytic center and forms a chiral enolate complex with the substrate to act as a photosensitive center in the reaction. The use of semi‐flow photochemical processes allowed a reduction in reaction time (24 h to 0.89 h) and good yields (up to 93%) and enantioselectivities (up to 88% ee) were obtained.magnified image

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Microreactors with multivariate external force field used for the chemical process intensification

Ma,

Zhao,

Tang

et al. 2024

Chemical Engineering Journal

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Sunlight assisted synthesis of α-aminonitrile using Capillary flow microreactor: A new approach

Cited by 8 publications

References 13 publications

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts

Visible‐Light‐Driven Enantioselective Aerobic Oxidation of β‐Dicarbonyl Compounds Catalyzed by Cinchona‐Derived Phase Transfer Catalysts in Batch and Semi‐Flow

Microreactors with multivariate external force field used for the chemical process intensification

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