33802-51-6

Upstream product

• 100-44-7 benzyl chloride 
• 107-12-0 propiononitrile 
• 645-59-0 dihydrocinnamonitrile 
• 74-88-4 methyl iodide 
• 673-32-5 1-Phenylprop-1-yne 
• 61540-41-8 Dimethyl-dithiocarbamic acid 1-cyano-1-methyl-2-phenyl-ethyl ester 
• 32755-48-9 (S)-2-Isocyano-2-methyl-3-phenyl-propionic acid ethyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 126-98-7 methacrylonitrile 
• 100-39-0 benzyl bromide 
• 108211-28-5 (R)-(-)-2-cyano-2-methyl-3-phenylpropionic acid 
• 100-51-6 benzyl alcohol 
• 1266802-94-1 potassium 2-cyanopropanoate 
• 884-90-2 benzyl diethyl phosphate 

Downstream Products

• 7499-19-6 2-methyl-2-phenylpropionamide 
• 31004-54-3 1.1-Dimethoxy-3-benzyl-3-cyan-butan 
• 18240-84-1 2-Methyl-2-benzyl-4.4-diethoxy-butyronitril 
• 259743-70-9 2-benzyl-2-methyl-3-phenylpropanenitrile 
• 18240-85-2 2-Benzyl-2-methyl-4-oxo-butyronitrile 
• 101441-53-6 3-ethyl-2-phenylquinoline 
• 84062-26-0 3-methyl-2-(4′-methylphenyl)quinoline 
• 959151-12-3 3-methyl-2-(3′-methylphenyl)quinoline 
• 5278-43-3 3-methyl-2-phenyl-quinoline 

Relevant academic research and scientific papers

Nickel/Cobalt-Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent

A Ni/Co co-catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the NiII pre-catalyst and vinyl nitriles, along with acting as the co-solvent in this reaction. Detailed mechanistic investigation supported a pathway via hydrocyanation of C≡C bond and the subsequent reduction of C=C bond. Wide substrate scope, the employment of a cheap and stable nickel salt as pre-catalyst, a safe cyano source and convenient experimental operation render this hydrocyanation practical for the laboratory synthesis of saturated nitriles. (Figure presented.).

A Titanium-Catalyzed Reductive α-Desulfonylation

A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.

Preparation of 2-arylquinolines from β-arylpropionitriles with aryllithiums and NIS through iminyl radical-mediated cyclization

Treatment of β-arylpropionitriles with aryllithiums, followed by the reaction with water and then with NIS under irradiation with a tungsten lamp gave 2-arylquinolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of imino-nitrogen-centered radicals, and their cyclization onto the aromatic rings of the imines to form 2-aryl-3,4-dihydroquinolines. Finally, the oxidation of 2-aryl-3,4-dihydroquinolines with NIS proceeds smoothly to generate 2-arylquinolines.

OXIDATIVE CONVERSION OF ALIPHATIC ALDEHYDES TO NITRILES USING OXOAMMONIUM SALT

The present invention relates to an oxidative transformation method of aliphatic benzaldehydes to nitriles using NH_4OAc through oxoammonium salts. By using stoichiometric amounts of oxoammonium salts to establish optimal reaction conditions associated with the oxidative conversion of aliphatic benzaldehydes to nitriles, high yields of nitrile can be selectively obtained, and the oxoammonium salts used can be oxidized and reused in a simple method.COPYRIGHT KIPO 2020

Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile

Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.

Enantioseparation of Sulfoxides and Nitriles by Inclusion Crystallization with Chiral Organic Salts Based on l-Phenylalanine

Enantioselective inclusion of aromatic sulfoxides and nitriles was achieved in a host framework created by organic salts comprising achiral benzoic acids and a chiral primary amine (1a) derived from l-phenylalanine. Tuning of the combined achiral acid component successfully changed the chiral recognition ability of the organic salts. The guest molecules were hydrogen-bonded to form three-component inclusion crystals, and the enantiomers of nitriles and sulfoxides were separated with high selectivity up to 92 and 98 % ee. As far as we know, this is the first example of the enantioseparation of non-functionalized aromatic nitriles.

Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes

Nucleophilic attack on carbon-based electrophiles is a central reactivity paradigm in chemistry and biology. The steric and electronic properties of the electrophile dictate its reactivity with different nucleophiles of interest, allowing the opportunity to fine-tune electrophiles for use as coupling partners in multistep organic synthesis or for covalent modification of proteins in drug discovery. Reactions that directly transform inexpensive chemical feedstocks into versatile carbon electrophiles would therefore be highly enabling. Herein, we report the catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and a bystanding N-F oxidant to furnish branched alkenyl nitriles that are difficult to prepare using existing methods. We show that the alkenyl nitrile products serve as electrophilic reaction partners for both organic synthesis and the chemical proteomic discovery of covalent protein ligands.

Process for the Catalytic Reversible Alkene-Nitrile Interconversion

The present invention refers to processes for catalytic reversible alkene-nitrile interconversion through controllable HCN-free transfer hydrocyanation.

Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate

An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.

α-Difluoromethylation on sp3 Carbon of Nitriles Using Fluoroform and Ruppert-Prakash Reagent

Difluoromethylation on sp3 carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the α-difluoromethylated nitrile products with an all-carbon q