Transformation of Alcohols into Nitriles under Electrocatalytic Oxidation Conditions

Кашпарова, В. П.; Shubina, E. N.; Il'chibaeva, I. B.; Kashparov, I. A.; Zhukova, I. Yu.; Каган, Е. Ш.

doi:10.1134/s1023193520050055

Cited by 7 publications

(3 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Aliphatic alcohols can be oxidized to the nitrile as the primary products using a 2/ potassium iodide/pyridine catalytic system (Scheme 44, II). 109 Selectivity was an issue with this system as some of the corresponding aldehyde was obtained as well. The conditions did not work for aryl alcohols, which did not oxidize beyond the aldehyde.…”

Section: Electrochemical Oxidation With Actmentioning

confidence: 99%

See 1 more Smart Citation

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Bray,

Stephens,

Weierbach

et al. 2023

Chem. Commun.

View full text Add to dashboard Cite

show abstract

Section: Electrochemical Oxidation With Actmentioning

confidence: 99%

“…Electrochemical oxidation of primary aliphatic alcohols. 108,109 Scheme 42 I. Synthesis of ACT functionalized polyethylene. II.…”

Section: Supramolecular Catalysismentioning

confidence: 99%

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Bray,

Stephens,

Weierbach

et al. 2023

Chem. Commun.

View full text Add to dashboard Cite

show abstract

“…The electrochemical one‐pot oxidation of a few alcohols was carried out in mild conditions in the presence of a 4‐Acetamido‐TEMPO‐iodine‐pyridine catalytic system in a bi‐phasic aqueous organic medium of methylene chloride‐aqueous sodium hydrocarbonate with platinum electrodes and hydroxylamine hydrochloride as a nitrogen source (Scheme 2). [103] The conventional routes to nitrile using alcohols include various methods like one‐pot synthesis involving transformation into the corresponding trifluoroacetate followed by a nucleophilic substitution reaction with sodium cyanide, [104] nickel‐catalyzed oxidation with tetrabutylammonium peroxydisulfate, [7] one‐pot syntheses with NH 3 catalyzed by a supported ruthenium hydroxide, [105] and aerobic double dehydrogenative catalysis [24] . These methods consist of drawbacks since they utilize heavy metal catalysts and organic solvents.…”

Section: Electrochemical Synthesis Of Nitrilesmentioning

confidence: 99%

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach

et al. 2022

View full text Add to dashboard Cite

Nitriles unveil widespread applications in pharmaceuticals, agrochemicals, textiles, rubber, polymers, and constitute a significant intermediate in several organic transformations, necessitating the design of simple and environmentally benign pathways for their synthesis. Over the recent years, electro‐organic reactions have found widespread attention in developing effective and selective organic synthesis. They possess several advantages: high atom economy, selectivity, minimal waste production, and shorter routes to multistep traditional organic reactions. The development of novel strategies for greener and sustainable electro‐organic synthesis of nitriles is therefore commendable. This review focuses on analyzing various methods and strategies used in the electrochemical synthesis of nitriles using phase transfer catalyst, N‐oxoammonium salts mediated electrocatalysis, iodine‐mediated electrocatalysis, and anodic oxidations of aldoximes. In addition, the recent trends including the synthesis of nitriles via C−H cyanation, domino oxidation, bio electrocatalysis, and metal‐ligand cooperative synthesis have been discussed.

show abstract