Direct oxidative conversion of benzylhalides, -amines, -alcohols, and arylaldehydes to nitriles with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane activated by NH4Br

Azarifar, Davood; Najminejad, Zohreh

doi:10.1007/s13738-014-0461-3

Cited by 11 publications

(1 citation statement)

References 60 publications

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“…Peroxide 2 has also been used as a stoichiometric reagent in a number of alternative transformations including the oxidation of alcohols to ketones, 25 oxidative cleavage of alkenes, 26 halogenation of aromatic rings, 27 epoxidation of -unsaturated carbonyl compounds, 28 oxidation of heterocycles 29 and the synthesis of nitriles. 30 Ongoing work within the laboratory to apply our knowledge to these transformations will be reported in due course.…”

Section: Discussionmentioning

confidence: 99%

Organocatalytic sulfoxidation

et al. 2021

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Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups.Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact.Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.

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Section: Discussionmentioning

confidence: 99%

Organocatalytic sulfoxidation

et al. 2021

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NH₃⋅H₂O: The Simplest Nitrogen‐Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water

Zhang

Zhao

et al. 2018

ChemistryOpen

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Aqueous ammonia (NH3⋅H2O) has been shown to serve as the simplest nitrogen‐containing ligand to effectively promote copper‐catalyzed selective alcohol oxidation under air in water. A series of alcohols with varying electronic and steric properties were selectively oxidized to aldehydes with up to 95 % yield. Notably, by increasing the amount of aqueous ammonia in neat water, the exclusive formation of aryl nitriles was also accomplished with good‐to‐excellent yields. Additionally, the catalytic system exhibits a high level of functional group tolerance with −OH, −NO2, esters, and heteroaryl groups all being amenable to the reaction conditions. This one‐pot and green oxidation protocol provides an important synthetic route for the selective preparation of either aldehydes or nitriles from commercially available alcohols.

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Deep eutectic solvent promoted one-pot synthesis of nitriles from alcohols

et al. 2020

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Direct oxidative conversion of benzylhalides, -amines, -alcohols, and arylaldehydes to nitriles with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane activated by NH4Br

Cited by 11 publications

References 60 publications

Organocatalytic sulfoxidation

Organocatalytic sulfoxidation

NH₃⋅H₂O: The Simplest Nitrogen‐Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water

Deep eutectic solvent promoted one-pot synthesis of nitriles from alcohols

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Direct oxidative conversion of benzylhalides, -amines, -alcohols, and arylaldehydes to nitriles with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane activated by NH4Br

Cited by 11 publications

References 60 publications

Organocatalytic sulfoxidation

Organocatalytic sulfoxidation

NH3⋅H2O: The Simplest Nitrogen‐Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water

Deep eutectic solvent promoted one-pot synthesis of nitriles from alcohols

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Product

Resources

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NH₃⋅H₂O: The Simplest Nitrogen‐Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water