C—F Bond Insertion into Indoles with CHBr2F: An Efficient Method to Synthesize Fluorinated Quinolines and Quinolones

Abstract

Comprehensive SummaryA 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 CHBr2F. The simple conditions, readily availability of CHBr2F, 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.