The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water

Göksu, Haydar; Orhan, Ersin

doi:10.1007/s12039-021-01926-1

Cited by 2 publications

(2 citation statements)

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“…The free HCl can be stabilized by IL in the form of H + and Cl – (Scheme a, electrostatic effect). The H + further promotes the protonation of the aldehyde group to generate I-a , and then reacts with NH 2 OH to generate oxime with high efficiency (Scheme b, polarization of aldehyde) . The oxime was protonated in the forms of I-b and I-c , on N with Cl – and on O with Cl – , respectively (Scheme c, polarization of oxime, electrostatic effect).…”

Section: Resultsmentioning

confidence: 99%

“…The H + further promotes the protonation of the aldehyde group to generate I-a 60,61 and then reacts with NH 2 OH to generate oxime with high efficiency (Scheme 2b, polarization of aldehyde). 62 The oxime was protonated in the forms of I-b and I-c, on N with Cl − and on O with Cl − , respectively (Scheme 2c, polarization of oxime, electrostatic effect). The enhanced nucleophilicity of the Cl − anion in the reaction system provides it with superior activity to attack the imine-H of I-c, resulting in the expulsion of H 2 O (Scheme 2d, nucleophilic attack).…”

Section: ■ Introductionmentioning

confidence: 99%

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Green Synthesis of Nitriles from Biomass-Derived Aldehydes by Evoking Intrinsic Cooperative Effects of Ionic Liquids

Li,

Shi,

Zhou

et al. 2024

ACS Sustainable Chem. Eng.

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Nitriles are important organic synthesis intermediates, but producing nitriles from renewable feedstocks with simple, efficient, and green catalytic systems is still challenging. Herein, we report a domino-type multiinteraction synergetic catalysis strategy for the synthesis of nitriles from aldehydes and hydroxylamine hydrochloride by using a simple ionic liquid (IL) (e.g., 1-butyl-3-methylimidazolium chloride, [BMIm][Cl]) as a catalyst. It is found that [BMIm][Cl] can tolerate various aliphatic and aromatic aldehydes containing different substituents, including a series of lignin-derived aldehydes, affording the corresponding nitriles in 66−99% yields under metal-/sulfur-/cyano-free conditions at 70 °C. Mechanistic investigations reveal that the acidic protons, polarization, electrostatic effect, hydrogen-bonding interactions, and nucleophilic attack all contribute to the generation of products. This strategy provides a green, simple, and efficient strategy to synthesize nitriles from biomass-derived aldehydes by an evoked multiple-interaction synergetic catalysis process from a simple [BMIm][Cl] ionic liquid catalyst.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%