99504-75-3

Upstream product

• 50907-23-8 1-bromo-4-(2H-tetrazol-5-yl)benzene 
• 1483-72-3 diphenyliodonium chloride 
• 50907-23-8 5-(4-bromophenyl)-1H-tetrazole 
• 98-80-6 phenylboronic acid 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 98321-11-0 C₁₃H₉BrN₂ 
• 203639-92-3 (R)-3-Methyl-2-[4-(2-phenyl-2H-tetrazol-5-yl)-benzenesulfonylamino]-butyric acid tert-butyl ester 
• 193809-84-6 (R)-3-(1H-Indol-3-yl)-2-[4-(2-phenyl-2H-tetrazol-5-yl)-benzenesulfonylamino]-propionic acid 
• 203640-02-2 (R)-3-(1H-Indol-3-yl)-2-[4-(2-phenyl-2H-tetrazol-5-yl)-benzenesulfonylamino]-propionic acid benzyl ester 
• 118794-95-9 5-(4-Bromo-phenyl)-3-methyl-2-phenyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

5-substituted-2-2H-tetrazoleamine manufacturing method

The present invention is a method for producing a 5-substituted-2-aryl-2H-tetrazole that is useful as an intermediate for producing a pharmaceutical compound, and relates to a method which selectively introduces an aryl group in the 2 position.

Cu(OH)(TMEDA)2Cl2-catalyzed regioselective 2-arylation of 5-substituted tetrazoles with boronic acids under mild conditions

A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regioselectively with a variety of arylboronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regioselective arylation of 5-alkyltetrazoles.

Regioselective arylation of N-tributylstannylated 5-substituted tetrazoles by diaryliodonium salts in the presence of Cu(OAc)2

The arylation of N-tributylstannylated 5-substituted tetrazoles with diaryliodonium salts at room temperature without base in CH2Cl2 in the presence of stoichiometric amounts of Cu(OAc)2 proceeds regioselectively at the N-

Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts

Palladium(0)-catalyzed arylation of 5-aryltetrazoles in t-BuOH at 80°C with diaryliodonium salts proceeds in the presence of copper(II) phenylcyclopropyl carboxylate regioselectively at the N2 position.