316-99-4

Upstream product

• 483-69-2 8-amino-5-(trifluoromethyl)quinoline 
• 316-76-7 8-nitro-5-trifluoromethyl-quinoline 
• 887144-94-7 Togni's reagent II 
• 33757-42-5 N-(quinolin-8-yl)acetamide 
• 2926-29-6 Langlois reagent 
• 2926-30-9 sodium triflate 
• 402-14-2 2-nitro-5-(trifluoromethyl)aniline 

Relevant academic research and scientific papers

C5-selective trifluoromethylation of 8-amino quinolines via photoredox catalysis

A new protocol for C5-selective C–H trifluoromethylation of 8-aminoquinolines via photoredox catalysis was developed. It allows rapid access to various C5-trifluoromethyl 8-amino quinoline derivatives in MeCN/H2O enabled by Eosin Y as photocatalysts.

Heterogeneous Chitosan@Copper(II)-Catalyzed Remote Trifluoromethylation of Aminoquinolines with the Langlois Reagent by Radical Cross-Coupling

The first remote C?H trifluoromethylation of N-(quinolin-8-yl)benzamide derivatives was accomplished with a user-friendly chitosan-based heterogeneous copper catalyst under mild conditions. The position-selective C?H activation protocol afforded the corresponding coupling products in good to excellent yields with excellent reusability of the catalyst by using the low-costing and stable Langlois reagent (CF3SO2Na) as the “CF3” source. Furthermore, control experiments suggested a single-electron-transfer process played a vital role in the heterogeneous C?CF3 cross-coupling.

Method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by utilizing micro-channel reaction device under visible light

The invention discloses a method for synthesizing C-5-bit trifluoromethylated 8-aminoquinoline by using a micro-channel reaction device under visible light. The method comprises the following steps: dissolving a 8-aminoquinoline compound in a solvent to obtain a homogeneous solution A, and dissolving eosin Y and NaCF3SO2 in water to obtain a homogeneous solution B; and simultaneously pumping the prepared homogeneous solution A and homogeneous solution B into a micro-mixer of a micro-channel reaction device respectively, mixing, introducing into a micro-channel reactor of the micro-channel reaction device under irradiation of visible light, making reaction, and washing separating, extracting, concentrating, and recrystallizinga reaction effluent, to obtain the product. According to the method, the product of C-5-bit trifluoromethylated 8-aminoquinoline is prepared by using a micro-channel reaction device under visible light irradiation, compared with common reaction, the reaction time is shortened, the reaction conversion rate is increased, and the product yield reaches 79%-93%; the product is stable and additive-free and is beneficial to large-scale production; meanwhile, operationis easy, the safety is high, and the defects of a traditional reaction kettle can be effectively overcome.

5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives

We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.