2‐Fluoro‐5‐nitrophenyldiazonium: A Novel Sanger‐Type Reagent for the Versatile Functionalization of Alcohols

As a novel Sanger‐type reagent, 2‐fluoro‐5‐nitrophenyldiazonium tetrafluoroborate enabled the versatile functionalization of primary and secondary aliphatic alcohols. Based on a mild nucleophilic aromatic substitution of the fluorine atom under unprecedented, base‐free conditions, the diazonium unit on the aromatic core of the resulting aryl‐alkyl ether could be employed for such diverse transformations as radical C−H activation and cyclization, as well as palladium catalyzed cross‐coupling reactions.