133205-47-7

Upstream product

• 13652-07-8 phenyltrifluorodiazoethane 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 13652-11-4 2,2,2‐trifluoro‐1‐phenylethan‐1‐one tosylhydrazone 
• 1666-96-2 3-phenylquinoline 
• 119197-24-9 3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 
• 137-07-5 2-amino-benzenethiol 

Relevant academic research and scientific papers

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds

The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound.

Synthesis of β-chloro(trifluoromethyl)acroleins and a specific reaction towards β-aminothiols

β-chloro-β-(trifluoromethyl)acroleins and β-chloro-α-(trifluoromethyl)-acrolein have been synthesized through Vilsmeier's reaction. A specific 1,4-addition of the nitrogen atom from β-aminothiols is observed.