Fluoroaromatics from Arylamines, a Convenient One-Pot Conversion Using Nitrosonium Tetrafluoroborate

Abstract

A simple, novel and extremely versatile procedure has been identified for the conversion of arylamines into the corresponding arylfluorides. The amine is treated with nitrosonium tetrafluoroborate in dichloromethane and the resulting diazonium tetrafluoroborate is heated, without isolation or drying, to give the fluoromatic, generally in good yield. The method is applicable even to arylamines bearing carboxyl and hydroxyl substituents which give poor yields of arylfluorides under Balz-Schiemann conditions.