91391-83-2

Upstream product

• 4177-16-6 2-vinylpyrazine 
• 98-80-6 phenylboronic acid 
• 71-43-2 benzene 
• 14508-49-7 2-chloropyrazin 
• 103-63-9 1-phenyl-2-bromoethane 
• 109-08-0 2-Methylpyrazine 
• 100-51-6 benzyl alcohol 
• 17376-04-4 2-phenethyl iodide 
• 32111-21-0 2-iodopyrazine 

Downstream Products

• 36680-26-9 styryl-pyrazine 
• 35782-35-5 trans-2-(2-phenylethenyl)pyrazine 

Relevant academic research and scientific papers

Manganese catalyzed C-alkylation of methylN-heteroarenes with primary alcohols

C-Alkylations of nine different classes of methyl-substitutedN-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(i)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon source. The diversifiedN-heteroarenes (41 examples) were isolated in high yields and selectivities. Water is produced as the sole byproduct, making the protocol environmentally benign.

Preparation method of alkyl/alkenyl substituted nitrogen-containing heterocyclic compound

The invention belongs to the technical field of organic synthesis, and particularly discloses a preparation method of an alkyl/alkenyl substituted nitrogen-containing heterocyclic compound, which comprises the following steps: (1) adding a 2-methyl nitrogen-containing heterocyclic compound, primary alcohol, alkali and an additive into an organic solvent, performing stirring reaction for 24 hours, and then cooling the product to room temperature; and (2) concentrating, separating and purifying the reaction liquid obtained in the step (1). The simple and effective method for preparing the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound under the metal-free and ligand-free conditions is realized, the 2-methyl nitrogen-containing heterocyclic compound and the primary alcohol which are economical and easy to obtain are used as raw materials, and the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound is prepared under the synergistic promotion of alkali and additives; and methyl alkylation and alkenylation reaction are carried out to generate the corresponding alkyl/alkenyl substituted nitrogen-containing heterocyclic compound. The product has high application value and can be used in the fields of spices, medicines, materials, organic synthesis and the like. The method is wide in application range, simple in process, green, simple, high in yield and suitable for popularization and application.

Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols

In this study, we developed a catalytic system for the C-alkylation of a methyl group on N-heteroaromatic compounds, including pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols based on a hydrogen-borrowing process with [Cp*IrCl2]2 (Cp*: η5-pentamethylcyclopentadienyl) combined with potassium t-butoxide and 18-crown-6-ether as the catalyst precursor.

Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcoholsviaC-H bond activation

The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping of the enamine intermediate1a'are of special importance.

Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes

This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.

Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: Direct access to functionalized N-heteroaromatics

Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety of methyl-substituted N-heteroarenes can be functionalized efficiently. To understand the mechanism of this reaction various kinetic and control experiments were carried out.

Application of novel coupling reaction to preparing carbon-carbon bond structured compounds

The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media

An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.

Nickel-catalysed alkylation of C(sp3)-H bonds with alcohols: direct access to functionalised N-heteroaromatics

The first base-metal catalysed coupling of primary alcohols with methyl-N-heteroaromatics is reported. The use of an earth abundant and nonprecious NiBr2/L1 system enables access to a series of C(sp3)-alkylated N-heteroaromatics. Mechanistic studies have established the participation of a hydrogen-borrowing strategy for α-alkylation.