140675-27-0

Upstream product

• 590-14-7 1-bromo-1-propene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 13154-14-8 1-propenylmagnesium bromide 
• 90921-33-8 4-(1-hydroxypropyl)benzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Downstream Products

• 60484-66-4 p-n-propylbenzonitrile 
• 619-65-8 4-cyanobenzoic Acid 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 95759-33-4 4-cyanocinnamaldehyde 

Relevant academic research and scientific papers

Enantio- and Regioselective NiH-Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides

A highly enantio- and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1-diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions.

Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates

A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.

Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis

A novel strategy involving visible-light-induced functionalization of alkenes for the synthesis of substituted aziridines was developed. The readily prepared N-protected 1-aminopyridinium salts were used for the generation of N-centered radicals. This approach allowed the synthesis of aziridines bearing various functional groups with excellent diastereoselectivity under mild conditions. Moreover, this protocol was successfully applied to prepare structurally diverse nitrogen-containing frameworks.

Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides

We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.

Palladium-catalyzed coupling reaction of alkenylgalliums with aryl halides

Treatment of aryl halides with alkenylgallium dichloride, prepared from GaCl3 and alkenylmagnesium bromide, in the presence of a catalytic amount of palladium provided cross-coupling products in good yields.

Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides

The electrochemical reduction of a mixture of aryl halides and activated alkyl halides in DMF in the presence of catalytic amount of NiBr2bipy leads to cross-coupling products in good to high yields. The method applies to the synthesis of α-aryl ketones, α-aryl esters, and allylated compounds from readily available organic halides. Optimization of the process has been obtained by slowly adding the most reactive organic halide (usually the activated alkyl halide) during the electrolysis which is best conducted at 70 °C when aryl bromides are involved.

The Stereochemistry of Rearrangements of Aryl and Hetaryl Groups to Primary Carbenic Centers

The products and stereochemistries of carbenic decompositions of varied 2-aryl-1-diazoalkanes and 1-diazo-2-(2-hetaryl)propanes have been determined.

The action of sodium hydrogen telluride on olefins

The action of sodium hydrogen telluride, NaTeH, on non electrophilic carbon-arbon double bonds has been investigated.The reaction is found to be very sensitive to the substituents on the ethylenic linkage. Whereas phenyl conjugated olefins are reduced to alkylbenzenes,the reagent adds to isolated mono and disubstituted double bonds leading to organotellurium derivatives and with gem-disubstituted ones it leads to a mixture of reduction and addition products. These results are interpreted in terms of a radical pair mechanism involving hydrogen atom transfer from hydrogen telluride,HTe- to the double bond.