1609401-41-3

Upstream product

• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 110-05-4 di-tert-butyl peroxide 
• 33757-49-2 4-methyl-N-(quinolin-8-yl)benzamide 
• 578-66-5 8-amino quinoline 
• 938-18-1 mesitylene-2-carboxylic acid chloride 
• 480-63-7 mesitylenecarboxylic acid 

Relevant academic research and scientific papers

Nickel-Catalyzed Ortho C–H Methylation of Aromatic Amides with Di-tert-butyl Peroxide as Methylation Reagent

A new efficient protocol for the ortho-methylation of benzamides with DTBP has been developed via Ni(II)-catalyzed C–H activation directed by 8-aminoquinoline. This method is performed under base-free, ligand-free conditions and utilizes cheap and commercially available reagents. Moreover, the by-product acetone derived from DTBP does not affect the purification of the product.

Copper-Catalyzed Intramolecular Benzylic C-H Amination for the Synthesis of Isoindolinones

A copper-catalyzed intramolecular amination occurs at the benzylic C-H of 2-methylbenzamides to deliver the corresponding isoindolinones of great interest in medicinal chemistry. The mild and abundant MnO2 works well as a terminal oxidant, and the reaction proceeds smoothly under potentially explosive organic peroxide-free conditions. Additionally, the directing-group-dependent divergent mechanisms are proposed: 8-aminoquinoline-containing benzamides include a Cu-mediated organometallic pathway whereas an aminyl radical-promoted Hofmann-Loffler-Freytag (HLF)-type mechanism can be operative in the case of N-naphthyl-substituted substrates.

C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane

An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale

Copper-Catalyzed Electrochemical Selective Bromination of 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent

A simple and mild protocol for copper-catalyzed bromination of quinoline at the C5 site of quinoline by anodic oxidation was developed, affording the desired remote C-H activation products with isolated yields of up to about 90%. The reaction proceeds wit

Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow

Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.

Nickel-Catalyzed Remote C4-H Arylation of 8-Aminoquinolines

A useful and convenient method for C-H bond arylation of 8-aminoquinoline motifs on the remote C4 position was developed. This method shows good functional group tolerance toward various Grignard reagents and aminoquinoline via a nickel catalysis, giving

Dicumyl Peroxide as a Methylating Reagent in the Ni-Catalyzed Methylation of Ortho C-H Bonds in Aromatic Amides

The direct methylation of ortho C-H bonds in aromatic amides with dicumyl peroxide (DCP) using a nickel complex as the catalyst is reported. The reaction shows a high functional group tolerance and is inhibited by radical scavengers. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bonds.

Isoindolone synthesis via palladium-catalysed intramolecular amination of benzylic C-H bonds

A new method for the construction of isoindolones is presented in this paper. Four 7-methyl-2-(8-quinolinyl)-2,3-dihydro-1Hisoindol-1-ones were synthesised from 2,6-dimethyl -N-(8-quinolinyl)benzamides via intramolecular direct amination of benzylic C-H bonds. This approach provides a convenient method affording structurally new isoindolones for medicinal chemistry research.