An efficient aerobic oxidative cyanation of tertiary amines with sodium cyanide using vanadium based systems as catalysts

Abstract

The first report on the use of vanadium-based catalysts for oxidative cyanation of tertiary amines with molecular oxygen in the presence of sodium cyanide and acetic acid to afford the corresponding alpha-aminonitriles in good to excellent yields is described.

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

“…Further, these bi-functional organic compounds having adjacent functional groups show dual reactivity as the nucleophilic addition provides an easy access to various compounds such as ␣-amino aldehydes, ketones and ␤-amino alcohols [20][21][22][23][24][25]. So far a number of metal-based catalysts, such as Fe [26][27][28], Ru [29,30], V [31], Mo [32], Au [33] and Re [34] in the presence of oxidants such as molecular oxygen, hydrogen peroxide, tert-butyl hydroperoxide (TBHP) have been reported for the direct oxidative cyanation of tertiary amines. Photoredox catalysts mainly based on ruthenium have also been reported for the oxidative ␣-cyanation of sp 3 C H bonds of tertiary amines [35][36][37][38].…”

Heterogeneously Catalyzed Oxidative Cyanation of Tertiary Amines with Sodium Cyanide/Hydrogen Peroxide using Polymer‐Supported Iron(II) Phthalocyanines as Catalyst

“…[8] However, tertiary amines can only be converted into a-amino nitriles by the oxidation with wastegenerating oxidants such as chlorine dioxide, [9] mchloroperbenzoic acid, [10] hydrogen peroxide [11] or mercuric acetate, [12] followed by the reaction of the iminium intermediate with cyanide ion. Oxidation with hypervalent iodine compounds, [13] metal-based catalysts such as iron salts, [14] V 2 O 5 [15] have also been reported. Furthermore, electrolysis of tertiary amines in methanol in the presence of sodium cyanide also provides an easy access to the a-amino nitriles.…”

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

“…However, the use of stoichiometric oxidants and production of huge amounts of hazardous waste is undesirable from environmental viewpoints. Metal-catalyzed oxidative of tertiary amines by using oxidants such as O 2 , H 2 O 2 , TBHP with NaCN in acetic acid is one of recently developed approaches for the direct synthesis of a-aminonitriles [19][20][21][22][23][24]. The generation of in situ HCN from the reaction of sodium cyanide and acetic acid is the common and critical feature of these methods.…”