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2‐Fluoro‐5‐nitrophenyldiazonium: A Novel Sanger‐Type Reagent for the Versatile Functionalization of Alcohols
Author(s) -
Fischer Oliver,
Heinrich Markus R.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100187
Subject(s) - chemistry , reagent , surface modification , tetrafluoroborate , aryl , alkyl , fluorine , primary (astronomy) , ether , combinatorial chemistry , organic chemistry , nucleophilic substitution , catalysis , nucleophile , palladium , base (topology) , polymer chemistry , ionic liquid , physics , astronomy , mathematical analysis , mathematics
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.