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Iodine Catalysis for C(sp 3 )–H Fluorination with a Nucleophilic Fluorine Source
Author(s) -
Bafaluy Daniel,
Georgieva Zoritsa,
Muñiz Kilian
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004902
Subject(s) - umpolung , chemistry , nucleophile , electrophile , bond cleavage , fluorine , radical , homolysis , catalysis , reagent , electrophilic fluorination , iodine , halogenation , medicinal chemistry , organic chemistry , photochemistry
Iodine catalysis was developed for aliphatic fluorination through light‐promoted homolytic C−H bond cleavage. The intermediary formation of amidyl radicals enables selective C−H functionalization via carbon‐centered radicals. For the subsequent C−F bond formation, previous methods have typically been limited by a requirement for electrophilic fluorine reagents. We here demonstrate that the intermediary instalment of a carbon–iodine bond sets the stage for an umpolung, thereby establishing an unprecedented nucleophilic fluorination pathway.