157671-45-9

Upstream product

• 506-68-3 bromocyane 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 143-33-9 sodium cyanide 
• 50-00-0 formaldehyd 
• 28363-24-8 2-((4-bromophenyl)amino)acetonitrile 
• 773837-37-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 140-29-4 phenylacetonitrile 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 124-38-9 carbon dioxide 
• 851199-50-3 C₉H₁₃BrN₂*ClH 
• 157671-32-4 (2E,4E)-2-(N-methyl-4-bromoanilino)-5-phenyl-2,4-pentadienenitrile 

Relevant academic research and scientific papers

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

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 α-aminonitriles in good to excellent yields is described

1-Cyano-3-(1H)-1,2-benziodoxols: Stable Cyanoiodinanes and Efficient Reagents for Direct N-Alkyl Cyanation of N,N-Dialkylarylamines.

Cyanobenziodoxol 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystaline compounds Cyanobenziodoxol 2 reacts with N,N-dimethylarylamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.

Acetone cyanohydrin: A convenient alternative of toxic sodium cyanide/acetic acid for oxidative cyanation of tertiary amines

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 α-aminonitriles in high yields with hydrog

Iron-Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines

This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines and its application in late-stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates and complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles and ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described catalyst system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Nano cobalt-copper ferrite catalyzed regioselective α-C(sp3)–H cyanation of amines: Secondary, tertiary, and drug molecules

Oxidative cyanation of sp3C–H bonds at the α position of amines was achieved using CoCuFe2O4 as a catalyst and NaCN as an inexpensive cyanide source at room temperature. CoCuFe2O4 was found to be an active catalyst for Csp [3]-Csp coupling, efficiently delivering valuable α-aminonitriles from tertiary/secondary amines in good yields. The corresponding products were obtained with high selectivity toward α position. In addition, functional group tolerance offered the opportunity for application in late-stage functionalization of biologically active molecules. This transformation proceeds convenient on a gram-scale, and the catalyst can be reused for several runs with consistent catalytic activity.

New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines

Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative α -cyanation of N-aryltetrahydroisoquinolines (THIQs) with trimethylsilyl cyanide (TMSCN), giving the corresponding products in good to excellent yields. Experime

Photoredox-Catalyzed Cα-H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

This paper describes the development and mechanistic studies of a general, high-yielding amine Cα-H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα-H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology. Mechanistic studies suggest that the carboxylic acid additive has three effects: formation of a stabilizing hemiaminal intermediate, prevention of catalyst decomposition by protonating the substrate, and modulation of fluorescence quenching of the photoexcited catalyst species.

Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source

The invention relates to a method for synthesizing alpha-aminonitrile by adopting AIBN as an individual cyan source. The method comprises the following steps: adding tertiary amine into a container, sequentially adding 2,2'-azodiisobutyronitrile (AIBN), p

Seven-coordinated chiral uranyl(VI) salen complex as effective catalyst for C–H bond activation of dialkylanilines under visible light

A new chiral uranyl(VI) complex incorporating a tetradentate salen ligand is reported. The synthesized uranyl complex is studied by microanalyses, spectroscopic and X-ray diffraction studies. The structural studies reveal a slightly distorted pentagonal bipyramid coordination environment around uranyl ion. Interestingly, the uranyl complex was found to be potential visible light active catalyst for C–H bond functionalization of dialkylanilines, and afforded moderate to excellent yield of corresponding α-aminonitriles when exposed to visible light for 8?h in the presence of NaCN and acetic acid as cyanide source, and H2O2as oxidant.