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α‐Cyanation of Aromatic Tertiary Amines using Ferricyanide as a Non‐Toxic Cyanide Source
Author(s) -
Nauth Alexander M.,
Otto Nicola,
Opatz Till
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500698
Subject(s) - cyanation , chemistry , ferricyanide , potassium ferricyanide , prussian blue , cyanide , potassium cyanide , salt (chemistry) , organic chemistry , inorganic chemistry , catalysis , electrochemistry , electrode
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.