A Practical and Cost-Efficient, One-Pot Conversion of Aldehydes into Nitriles Mediated by ‘Activated DMSO’

Augustine, John Kallikat; Bombrun, Agnès; Atta, Rajendra Nath

doi:10.1055/s-0030-1261181

Cited by 43 publications

(23 citation statements)

References 2 publications

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“…The TAAa ldehyde from the previous step was converted to the TAAn itrile by the reported method. [26] A1 00 mL round-bottomed flask was charged with am ixture of N,N-bis(4-formylphenyl)-4-iodoaniline (1.5 g, 3.5 mmol) and hydroxylamine hydrochloride (0.61 g, 8.7 mmol) in DMSO (8 mL). The mixture was stirred at 80 8C for 4h.T he progress of the reaction was monitored by TLC.…”

Section: Synthesis Of 1-8mentioning

confidence: 99%

Solution‐Processable Unsymmetrical Triarylamines: Towards High Mobility and ON/OFF Ratio in Bottom‐Gated OFETs

Dheepika

Imran

Bhuvanesh

et al. 2019

Chemistry A European J

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Self‐assembly of organic small molecules into an ordered thin film has been the key strategy towards efficient charge transport for organic field‐effect transistors (OFETs). Solution processing is a feasible and economic way to enhance pi–pi interaction. Herein, nitrile‐substituted unsymmetrical triarylamines for OFET applications with high mobility are reported. The compounds were constructed by Suzuki cross‐coupling reactions under inert conditions. The HOMO level of about 5.3 eV indicates good hole‐transporting ability. OFETs were assembled in bottom‐gate, top‐contact architecture. Devices fabricated from a binary solvent system exhibited excellent p‐channel characteristics, with impressively high charge‐carrier mobility of up to 2.58 cm2 V−1 s−1 and ION/OFF current ratios of 106–107. SEM and AFM analysis showed the efficient molecular self‐assembly attained by the simple and effective solvent‐engineering method. Theoretical insights obtained by DFT calculations supported by single‐crystal structures showed that the crystalline nature and packing modes of these compounds ensure high mobility. The results prove that these compounds have great potential for use in numerous electronic applications, such as sensors and logic switches.

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Section: Synthesis Of 1-8mentioning

confidence: 99%

Solution‐Processable Unsymmetrical Triarylamines: Towards High Mobility and ON/OFF Ratio in Bottom‐Gated OFETs

Dheepika

Imran

Bhuvanesh

et al. 2019

Chemistry A European J

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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 . The XtalFluor‐E reagent reported by Paquin offers a mild method for dehydration of oximes (reaction 2, Figure ) .…”

Section: Figurementioning

confidence: 99%

“…[12] These syntheses require highly toxic metal cyanides, elevated temperature, and introduce an additional carbon atom from the cyanide nucleophile.N itriles can also be obtained from alcohols, [13][14][15][16] amines, [17,18] amides, [19][20][21] and aldoximes. [22][23][24] However,these methods often requireh igh temperature, metal catalysts,a nd strong oxidizingr eagents.…”

mentioning

confidence: 99%

“…[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). [28] However,i ts high reactivity with primary amides and alcohols makes it incompatible with these functionalities.…”

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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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“…2,[5][6][7][8][9][10][11][12][13] However, oxidation of alcohols in continuous flow using RuO 2 /Al 2 O 3 catalysts has been previously reported. 2,[5][6][7][8][9][10][11][12][13] However, oxidation of alcohols in continuous flow using RuO 2 /Al 2 O 3 catalysts has been previously reported.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic insights into the oxidative dehydrogenation of amines to nitriles in continuous flow

Corker

Ruiz‐Martínez

Riisager

et al. 2015

Catal. Sci. Technol.

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The oxidative dehydrogenation of various aliphatic amines to their corresponding nitrile compounds using RuO 2 /Al 2 O 3 catalysts in air was successfully applied to a continuous flow reaction. Conversions of amines (up to >99%) and yields of nitriles (up to 77%) varied depending on reaction conditions and the amine utilised. The presence of water was found to be important for the activity and stability of the RuO 2 /Al 2 O 3 catalyst. The Hammett relationship and in situ infrared spectroscopy were applied to divulge details about the catalytic mechanism of the oxidative dehydrogenation of amines over RuO 2 /Al 2 O 3 catalysts.Catal. Sci. Technol. This journal is Fig. 1 Mechanism for the oxidative dehydrogenation of amines by RuO 2 /Al 2 O 3 catalysts, proposed by Mizuno et al. 13

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A Practical and Cost-Efficient, One-Pot Conversion of Aldehydes into Nitriles Mediated by ‘Activated DMSO’

Cited by 43 publications

References 2 publications

Solution‐Processable Unsymmetrical Triarylamines: Towards High Mobility and ON/OFF Ratio in Bottom‐Gated OFETs

Solution‐Processable Unsymmetrical Triarylamines: Towards High Mobility and ON/OFF Ratio in Bottom‐Gated OFETs

Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Mechanistic insights into the oxidative dehydrogenation of amines to nitriles in continuous flow

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