36146-27-7

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 94-36-0 dibenzoyl peroxide 
• 98-80-6 phenylboronic acid 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 1008-88-4 3-phenylpyridine 
• 7677-24-9 trimethylsilyl cyanide 
• 108-86-1 bromobenzene 

Downstream Products

• 1335110-60-5 3,5-diphenylpyridine-4-carbonitrile 

Relevant academic research and scientific papers

Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant

A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.

C?H Cyanation of 6-Ring N-Containing Heteroaromatics

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.

Pyridine derivatives directly aromatise process (by machine translation)

The invention relates to the technical field of preparation processes of aromatic pyridine derivatives, and in particular relates to a direct aromatization process of a pyridine derivative. The process comprises the following flows of adding the pyridine derivative, arylboronic acid, ferrite and trifluoroacetic acid to a flask in sequence, stirring the mixture uniformly at room temperature, adding persulfate, continuing stirring, and filtering, extracting, concentrating and separating the obtained product after reaction is completed, thus obtaining the aromatized pyridine derivative. The direct aromatization process has the beneficial effects that ferrite is adopted as a catalyst, persulfate is adopted as an oxidant, arylboronic acid is promoted to generate aryl free radicals in the persulfate radical and ferrous oxide ion reaction process, and the aryl free radicals are added to the pyridine derivative, thus obtaining the corresponding product; the direct aromatization process is relatively low in production cost and relatively high in reaction yield, and is suitable for popularization and use.

Lewis acid-catalyzed borono-minisci reactions of arylboronic acids and heterocycles

A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Br?nsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.

Scope and limitation for FeSO4-mediated direct arylation of heteroarenes with arylboronic acids and its synthetic applications

FeSO4-mediated direct arylation of heteroarenes with arylboronic acids in the presence of K2S2O8 has been developed. A slow addition of an aqueous solution of an iron complex was crucial in the arylation. Scope and limitation of the heteroarenes and arylboronic acids are discussed. Furthermore, the direct arylation was applied to the formal total synthesis botryllazine B and sodium channel inhibitor.

Direct arylation of substituted pyridines with arylboronic acids catalyzed by iron(II) oxalate

The direct arylation of substituted pyridines with several arylboronic acids has been developed. This transformation could proceed readily at ambient temperature using inexpensive reagents: iron(II) oxalate as a catalyst, potassium persulfate as a co-oxidant, which can afford the arylated products in mild to good yields. The mechanism is presumed to proceed through a nucleophilic radical addition to the pyridines with in situ reoxidation.

Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway

A novel iron-mediated direct C-H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.

C-H arylation of pyridines: High regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring

We report a new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO2, CN, F and Cl). The new protocol expands the scope of catalytic azine functi

DECOMPOSITION DU PEROXYDE DE BENZOYLE DANS LES MELANGES BENZENE/X-4 PYRIDINES (X=CH3, H, CN). ETUDE CINETIQUE ET INFLUENCE DES SUBSTITUANTS SUR LA REACTIVITE NUCLEOPHILE ET RADICALAIRE DE L'ATOME D'AZOTE

Effect of a 4-substituent in the pyridine ring upon the decomposition kinetics of benzoyl peroxide in 4-X pyridine/benzene binary mixtures (X=CH3,H,CN) has been studied.The second-order rate constant for the pyridine-induced decomposition was 2x10-6 lmol-1s-1 and in 4-methylpyridine it was 10-5 lmol-1s-1, a five-fold increase, whereas there was no nucleophilic attack on the peroxide oxygen atoms of benzoyl peroxide by 4-cyanopyridine.The surprisingly high increase of the radical-induced decomposition in 4-cyanopyridine might result from the attack at the nitrogen atom of the pyridine ring by the phenyl radical, the 1-phenylpyridinyl radical being stabilized by the cyano group.