Straightforward zinc-catalyzed transformation of aldehydes and hydroxylamine hydrochloride to nitriles

Enthaler, Stephan; Weidauer, Maik; Schröder, Fanny

doi:10.1016/j.tetlet.2011.12.036

Cited by 40 publications

(13 citation statements)

References 37 publications

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“…Dehydration of oximes is perhaps the most straightforward method of nitrile synthesis (reaction 1, Figure ) . However, the use of high boiling solvents, acidic medium, high temperature and oxidizing conditions limit the scope of these dehydrations and result in side reactions .…”

Section: Figurementioning

confidence: 99%

“…Dehydrationo fo ximes is perhaps the most straightforward method of nitrile synthesis (reaction 1,Figure2). [25][26][27][28] However, the use of high boilings olvents, acidic medium, high temperature and oxidizing conditions limit the scope of these dehydrations and result in side reactions. [24] The XtalFluor-E reagent reportedb yP aquin offersamild method for dehydration of oximes (reaction 2, Figure 2).…”

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confidence: 99%

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Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Gurjar

Bater

Fokin

2019

Chemistry A European J

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Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one‐pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.

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Section: Figurementioning

confidence: 99%

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confidence: 99%

Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Gurjar

Bater

Fokin

2019

Chemistry A European J

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“…Due to the importance of nitrile compounds, following their previous work on zinc‐catalyzed dehydration of primary amides to nitriles with N ‐methyl‐ N ‐(trimethylsilyl)trifluoroacetamide (MSTFA), in 2011 Enthaler et al. developed a new method to prepare nitriles from aldehydes together with hydroxylamine hydrochloride in one pot (Scheme ) . Several zinc salts were found to be efficient in this oxidative transformation.…”

Section: Oxidative Transformation Of Aldehydesmentioning

confidence: 99%

Toward Greener Oxidative Transformations: Base‐Metal Catalysts and Metal‐Free Reactions

2015

The Chemical Record

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“…Enthaler et al 20 presented a direct conversion of benzaldehyde to benzonitrile catalyzed by Zn(CH 3 COO) 2 (5 mol%). When benzaldehyde was 0.72 mmol, n(benzaldehyde) : n(NH 2 -OH$HCl) ¼ 1 : 1.2, toluene was 2 mL, reaction temperature was 100 C, reaction time was 24 h, the benzonitrile yield was 79.0%.…”

Section: Introductionmentioning

confidence: 99%