C—F Bond Insertion into Indoles with <scp>CHBr<sub>2</sub>F</scp>: An Efficient Method to Synthesize Fluorinated Quinolines and Quinolones
Chao Li, Lei Chen, Hongye Wang, Zixi Yan, Bin Lyu, Weiping Lyu, Changwei Jiang, Dehua Lu, Jiaxing Li, Ning Jiao, Song Song
Abstract
Comprehensive Summary A mild and practical method for synthesizing fluorinated quinoline derivatives, which have a wide range of applications in pharmaceuticals, materials, and organic synthesis, was described through C—F bond insertion into indoles using CHBr 2 F. The simple conditions, readily availability of CHBr 2 F, as well as the versatility of the transformations make this strategy very powerful in synthesizing 3‐fluoroquinoline and 3‐fluoroquinolone. The mechanistic studies reveal that bromofluorocarbene generated in‐situ under basic condition was the key intermediate.
Topics & Concepts
ChemistryQuinolineCombinatorial chemistryNanotechnologyOrganic chemistryMaterials scienceFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Reactions of Organic Compounds