14788-57-9

Upstream product

• 98-88-4 benzoyl chloride 
• 14148-44-8 8-(N-methylamino)quinoline 
• 100-21-0 terephthalic acid 
• 74-88-4 methyl iodide 
• 65-85-0 benzoic acid 
• 33757-48-1 N-quinolin-8-yl-benzamide 

Relevant academic research and scientific papers

A First Example of Cobalt-Catalyzed Remote C H Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism

The development of new C H functionalization protocols based on inexpensive cobalt catalysts is currently attracting significant interest. Functionalized 8-aminoquinoline compounds are high-potential building blocks in organic chemistry and pharmaceutical compounds and new facile routes for their preparation would be highly valuable. Recently, copper has been applied as catalyst for the functionalization of 8-aminoquinoline compounds and found to operate through a single electron transfer (SET) mechanism, although requiring elevated reaction temperatures. Herein, we described the first example of a cobalt-catalyzed remote C H functionalization of 8-aminoquinoline compounds operating through a SET mechanism, exemplified using a practical and mild nitration protocol. The reaction uses inexpensive cobalt nitrate hexahydrate [Co(NO3)2?6 H2O] as catalyst and tert-butyl nitrite (TBN) as nitro source. This methodology offers the basis for the facile preparation of many new functionalized 8-aminoquinoline derivatives. (Figure presented.).

Selective C-C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant

Herein, copper-catalyzed direct C-C bond cleavage of amides fused to 8-aminoquinoline as a directing group to form urea in the presence of amines and dioxygen is reported. Compared to the previous C-H aminations of amides via C-H activation, this reaction presents a catalyst and oxidant controlled C-C bond cleavage strategy that enables amidation through a radical process. CuBr/Ag2CO3/O2 shows the best catalytic result at 150 °C. A series of aryl and alkyl amides were compatible with this transformation. Notably, this method provided access to cyclohexanone, one of the most important industrial materials. The pathway of this reaction was investigated.

Iron-Catalyzed Regioselective Remote C(sp2)-H Carboxylation of Naphthyl and Quinoline Amides

Iron(III)-catalyzed regioselective direct remote C-H carboxylation of naphthyl and quinoline amides was developed using CBr4 and alcohol. The reaction involves a radical pathway using a coordination activation strategy and single electron transfer process. The use of sustainable iron catalysis, selectivity, and the substrate scope are the important practical features.

Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow

An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhyda

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

From Surprising Solvothermal Reaction to Uncommon Zinc(II)-Catalyzed Aromatic C-H Activation Reaction for Direct Nitroquinoline Synthesis

In this work, we first found a surprising solvothermal reaction for direct dinitration of quinoline derivative. To explore the application in direct nitroquinoline synthesis, this reaction was subsequently modified as an equivalent reaction in a Schlenk tube. More significantly, after a constant attempt, nitrated derivative was obtained in optimized condition with a zinc(II) sulfate catalyst, where some substrates with strong electron-withdrawing group were first nitrated by a directly catalyzed condition. This new zinc(II)-catalyzed aromatic C-H activation reaction is the first example of direct dinitration by a single catalyst, which will be a new facile and environmentally friendly strategy to access synthetically useful nitroquinoline derivative.

Regiodivergent Visible Light-Induced C–H Functionalization of Quinolines at C-5 and C-8 under Metal-, Photosensitizer- and Oxidant-Free Conditions

A general strategy towards the selective perfluoroalkylation of quinoline derivatives at C-5 and C-8 is described. This exceptionally mild radical transformation, compatible with a large panel of substrates, does not require any transition metal catalysts or oxidants. Outstandingly, visible light photoinduction using simple household bulbs, in the absence of a photosensitizer, is the unique activation mode. Further importance of this reaction relies on its capacity to functionalize selectively both C-5 and C-8 positions of quinolines. This transformation, perfectly fulfilling green chemistry requirements, allows a truly practical and straightforward access to a variety of unprecedented functionalized amino- and amidoquinoline skeletons, presenting attractive features for medicinal and agrochemical industry. (Figure presented.).

Ligand-enabled, copper-promoted regio- and chemoselective hydroxylation of arenes, aryl halides, and aryl methyl ethers

We report here a practical method for the ortho C-H hydroxylation of benzamides with inexpensive copper(II) acetate monohydrate and a pyridine ligand. An intra- and intermolecular ligand combination was explored to achieve regio- and chemoselective hydroxylation. Interestingly, typical regiochemical scrambling associated with the C-H activation was further resolved by introducing a ligand-directed ortho hydroxylation of haloarenes and aryl methyl ethers.