20132-76-7

Upstream product

• 109-75-1 but-3-enenitrile 
• 71-43-2 benzene 
• 14368-40-2 3-phenyl-2-butenonitrile 
• 14368-40-2 (E)-3-phenyl-2-butenenitrile 
• 107-13-1 acrylonitrile 
• 75-05-8 acetonitrile 
• 98-86-2 acetophenone 
• 100-41-4 ethylbenzene 
• 4786-20-3 crotononitrile 
• 2996-92-1 phenyl trimethylsiloxane 
• 98-85-1 1-Phenylethanol 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 2942-58-7 diethyl cyanophosphonate 
• 318515-74-1 3-phenylcyclobutan-1-one O-benzoyl oxime 

Downstream Products

• 38135-56-7 (3-phenyl-n-butyl)-amine 
• 874993-81-4 ethyl 3-phenylbutanimidoate hydrochloride 
• 1018986-04-3 2-(1-phenylethyl)pent-4-enenitrile 
• 14368-40-2 (Z)-3-phenylbut-2-enenitrile 
• 14368-40-2 (E)-3-phenyl-2-butenenitrile 

Relevant academic research and scientific papers

Syngas Instead of Hydrogen Gas as a Reducing Agent─A Strategy To Improve the Selectivity and Efficiency of Organometallic Catalysts

Catalytic reduction reactions play a major role in modern chemistry and are often based on hydrogen gas as a reducing agent. However, the high reactivity of hydrogen is often accompanied by low selectivity on the simple catalysts. Herein, we showed that the usage of syngas as a reducing agent can be a more efficient and selective strategy. Based on control experiments, a plausible mechanism was proposed to explain the superior performance of syngas. The versatility of this approach was demonstrated by successful application to three reactions using different metal catalysts: direct reductive amination, reductive esterification, and the tandem CH-reductive alkylation-hydrolysis-decarboxylation. Catalyst turnover numbers up to 30,000 were achieved. Moreover, the developed strategy showed improved selectivity and functional group compatibility as compared to the use of hydrogen gas.

Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel

Nickel-catalyzed asymmetric hydrogenation of several types of alkenes proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. The scope of alkenes herein include α,β-unsaturated esters, n

A photocatalytic sp3 C-S, C-Se and C-B bond formation through C-C bond cleavage of cycloketone oxime esters

The photocatalytic thiolation, selenylation and borylation of cycloketone oxime esters through iminyl radical-triggered C-C bond cleavage were described. The reactions provide a unified approach to alkyl sulfur, selenium and boron compounds tethered to a

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.

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.

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.

Photocatalytic Neophyl Rearrangement and Reduction of Distal Carbon Radicals by Iminyl Radical-Mediated C?C Bond Cleavage

The control of selectivity in the reactions of the highly reactive open-shell carbon radicals is an attractive but often challenging task. Building on the strategy of photoinduced iminyl radical-mediated C?C bond cleavage, we have developed photocatalytic neophyl rearrangement and reduction of distal carbon radicals under visible light irradiation of O-acyl oximes. This mild protocol tolerates a wide range of readily available O-acyl oximes, enabling facile synthesis of diversely substituted α,β-unsaturated nitriles and β-functionalized saturated nitriles in a highly selective manner. (Figure presented.).

A strategy for generating aryl radicals from arylborates through organic photoredox catalysis: Photo-Meerwein type arylation of electron-deficient alkenes

Photoinduced reactions of arylboronic acids with electron deficient alkenes under mild organic photoredox catalysis conditions lead to the formation of Meerwein arylation type adducts via the generation of aryl radicals.

A Visible-Light-Driven Iminyl Radical-Mediated C?C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters

A room-temperature, visible-light-driven N-centered iminyl radical-mediated and redox-neutral C?C single bond cleavage/radical addition cascade reaction of oxime esters and unsaturated systems has been accomplished. The strategy tolerates a wide range of O-acyl oximes and unsaturated systems, such as alkenes, silyl enol ethers, alkynes, and isonitrile, enabling highly selective formation of various chemical bonds. This method thus provides an efficient approach to various diversely substituted cyano-containing alkenes, ketones, carbocycles, and heterocycles.

Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach

A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.