Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water

Quinn, Dylan J.; Haun, Graham J.; Moura‐Letts, Gustavo

doi:10.1016/j.tetlet.2016.07.047

Cited by 49 publications

(21 citation statements)

References 43 publications

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“…It was observed that the reaction is exothermic as indicated by the sudden rise in temperature from the set temperature when the samples were microwaved from 50 °C onwards. m-NBA is reported to take long reaction time [19] while here it took 10 minutes for completion. Other aldehydes took only 5 minutes.…”

Section: Optimisation Of Reaction Condition In Microwave Reactormentioning

confidence: 81%

“…Later, several other methods and reagents have been employed for conversion of aldehydes to nitrile via their aldoximes [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Recently, oxoammonium salts [18], hydroxylamine-o-sulphonic acid [19], and o-(diphenyl phosphinyl)hydroxylamine / toluene [20], were reported. In addition, Fe3O4 nanoparticles [21] and active silver nanoparticles [22] were used as catalyst.…”

Section: Introductionmentioning

confidence: 99%

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Microwave assisted one pot conversion of aromatic aldehydes to nitriles

et al. 2018

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Nitriles are versatile organic precursors in organic synthesis and have numerous applications. An efficient microwave assisted method for conversion of aromatic aldehydes to the corresponding nitriles is reported. Aldehydes are readily converted to oxime followed by acetylation and acetic acid elimination to provide nitriles in good yields within minutes. The method proved to be efficient for the synthesis of aromatic and heterocyclic nitriles. The reaction proceeds smoothly by microwave at 150 °C for 5 minutes. The obtained products are isolated simply by filtration or extraction.

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Section: Optimisation Of Reaction Condition In Microwave Reactormentioning

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Microwave assisted one pot conversion of aromatic aldehydes to nitriles

et al. 2018

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“…In the laboratory setting, it has been used for the synthesis of arylfluorosulfates and fluorosulfonates for the sulfur(VI) fluoride exchange (SuFEx) chemistry, and as a triflate surrogate in coupling reactions . Likewise, hydroxylamine hydrochloride is a stable and inexpensive reagent in contrast to other hydroxylamine derivatives such as O ‐mesitylsulfonylhydroxylamine (MSH) and NH 2 OSO 3 H …”

Section: Figurementioning

confidence: 99%

“…[36] In the laboratory setting, it has been used for the synthesis of arylfluorosulfates and fluorosulfonates for the sulfur(VI) fluoride exchange (SuFEx) chemistry, [37,38] and as at riflate surrogate in coupling reactions. [39][40][41][42][43] Likewise, hydroxylamine hydrochloride is as table and inexpensive reagent in contrast to other hydroxylamine derivatives such as O-mesitylsulfonylhydroxylamine (MSH) [44] and NH 2 OSO 3 H. [45] As shown in reaction 4( Scheme 1), our early investigation established the feasibility of this approach. The oxime of picolinaldehyde was converted to the corresponding nitrile in nearly quantitative yield upon treatment with SO 2 F 2 in the presence of triethylamine.…”

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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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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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“…1,2 Nitriles have been widely utilised as synthetic intermediates for pharmaceuticals, agricultural chemicals, dyes and material sciences, and some nitriles have seen direct use as pesticides, perfumes, metal inhibitors and liquid crystal materials. [3][4][5] For these reasons, much attention has been paid to the development of efficient and practical methods for their synthesis. There are diverse methods for the synthesis of nitrile groups from different organic functional groups.…”

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confidence: 99%