α-Cyanation of Aromatic Tertiary Amines using Ferricyanide as a Non-Toxic Cyanide Source

The reaction of aromatic tertiary amines with potassium ferricyanide directly provides the useful α‐amino nitriles. The inexpensive iron complex functions both as an oxidant and as a cyanide source. The presence of molecular oxygen speeds up the reaction which can be performed in aqueous tert‐butano...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-11, Vol.357 (16-17), p.3424-3428
Main Authors: Nauth, Alexander M., Otto, Nicola, Opatz, Till
Format: Article
Language:English
Subjects:
Amines
Catalysis
cross-dehydrogenative coupling
Cyanides
CH activation
green chemistry
Potassium ferricyanide
Tables (data)
Toxic
Toxicity
Toxicology
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Summary:The reaction of aromatic tertiary amines with potassium ferricyanide directly provides the useful α‐amino nitriles. The inexpensive iron complex functions both as an oxidant and as a cyanide source. The presence of molecular oxygen speeds up the reaction which can be performed in aqueous tert‐butanol or even in ethanol‐based mixtures like Tequila. While amine cyanations usually employ highly toxic cyanide sources, potassium ferricyanide is even less toxic than table salt. No expensive metal complexes are required as catalysts and the co‐product of the cyanation, Prussian blue, has no known toxicity and is rather used as an antidote.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500698