Acetone Cyanohydrin: A Convenient Alternative of Toxic Sodium Cyanide/Acetic Acid for Oxidative Cyanation of Tertiary Amines

Abstract

Acetone cyanohydrin was found to be a facile, convenient and comparatively safer alternative to toxic sodium cyanide/acetic acid system for generating in situ HCN for the oxidative cyanation of tertiary amines to a-aminonitriles in high yields with hydrogen peroxide using RuCl 3 as catalyst. In addition organic nature of acetone cyanohydrin makes it more suitable for an organic transformation since it is readily soluble in reaction medium and can be added in a controlled manner.

PEGylated magnetic nanoparticles (PEG@Fe 3 O 4 ) as cost effective alternative for oxidative cyanation of tertiary amines via C H activation

“…In continuation to our efforts towards developing efficient and cost-effective methodologies for organic transformations [39][40][41], herein we report a facile, highly efficient and selective method for the oxidative cyanation of tertiary amines via C H bond activation using PEGylated magnetic nanoparticles as catalyst in the presence of hydrogen peroxide as oxidant and NaCN in acetic acid as a cyanide source (Scheme 1). Furthermore, facile recovery of the catalyst with the use of an external magnet makes the developed method attractive for wider applications.…”

Multifunctional Nitrogen‐Doped Carbon Nanodots for Photoluminescence, Sensor, and Visible‐Light‐Induced H2 Production

“…Numerous transition metals (Ru,17 Cu,18 V,19 Au,20 Mo,21 Co22) without or with ligands have been employed as catalysts for the amine cyanation in combination with peroxides or molecular oxygen as oxidants. Cheap sodium or potassium cyanide worked excellently as cyanide sources, but efforts were also undertaken to use less toxic cyanation reagents, such as trimethylsilyl cyanide,23 cyanohydrins,24 ethyl cyanoformate,25 or malononitrile 18…”

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

“…Thus, the authors came to the conclusion that the higher yields of cyanation product obtained in the case of the hydrogen peroxide system was due to the highly reactive oxoruthenium species and low-valence ruthenium species. Sain et al disclosed a new methodology towards the oxidative cyanation of tertiary amines using Ru as the catalyst (Scheme 11) [35]. In this reaction, the comparatively safer acetone cyanohydrin was utilized as the cyanating agent.…”

“…Sain et al disclosed a new methodology towards the oxidative cyanation of tertiary amines using Ru as the catalyst ( Scheme 11 ) [ 35 ]. In this reaction, the comparatively safer acetone cyanohydrin was utilized as the cyanating agent.…”