Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation

Abstract

In recent years, oxidative dehydrogenation (ODH) of amines has proven to be an efficient, clean and fundamental route for the synthesis of nitriles. This review focuses on the different types of reactions for the oxidation of amines to nitriles such as transition metal-catalysis, photoactivation, acceptorless dehydrogenation, nitroxyl radical-mediated, and N,O-doped mesoporous carbon. Emphasis is placed on the ODH of amines to the corresponding nitriles using ruthenium catalysts. Metal free systems utilizing iodine, TEMPO and its derivatives, TCCA with or without additives are also discussed. The ODH of amines using N,O-doped mesoporous carbon is elaborated. Attention is also given to major improvements, achievements, and challenges that still remain in the field of nitrile synthesis from amines. 2.3. Photocatalytic System 2.4. Acceptorless Dehydrogenation (AD) 2.5. Substrate Scope and Functional Group Tolerance 3.

Electrochemical Dehydrogenation Pathways of Amines to Nitriles on NiOOH

“… 3 , 5 − 8 While these methods are greener than the traditional nitrile synthesis methods and offer several important advantages, there are still challenges that must be overcome, with most methods facing some combination of drawbacks including low turnover numbers, requiring the use of elevated temperatures and O 2 pressures, or requiring the use of complex ligands and catalysts that can be challenging or expensive to produce. 3 , 5 , 9 Furthermore, side reactivity can be an issue, often stemming from the electrophilic imine intermediate undergoing a nucleophilic attack before it can undergo dehydrogenation to form the nitrile. 2 , 5 , 9 …”

“… 3 , 5 , 9 Furthermore, side reactivity can be an issue, often stemming from the electrophilic imine intermediate undergoing a nucleophilic attack before it can undergo dehydrogenation to form the nitrile. 2 , 5 , 9 …”

Production of Nitrogen‐Containing Compounds via the Conversion of Natural Microalgae from Water Blooms Catalyzed by ZrO2

“…The common methods for preparing nitriles include amide dehydration and cyanidation of halogenated hydrocarbons. The cyanation of halogenated hydrocarbons is restricted by the use of highly toxic cyanide ions [34] . Although petroleum is still the main resource for the production of amides and nitriles, actively looking for renewable resources to produce them can help to reduce greenhouse gas emissions and contribute to sustainable development [35] .…”

A Versatile Light‐Triggered Radical‐Releasing Surface Coating Technology

“…[ 8 ] While nitroxides have been utilized extensively as catalysts to make new molecules and materials, [ 9–11 ] new materials are being developed from nitroxides to provide new structures with unique redox activity. [ 12 ] Some of these applications include organic electronics, [ 13 ] energy storage, [ 14,15 ] OLEDs, [ 16 ] heterogeneous catalysis, [ 11,17,18 ] and spintronics. [ 19 ] While the previously mentioned applications use nitroxides to mediate the transport of electrons, they can also be used to modulate the production and concentration of reactive oxygen species (ROS).…”