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Benzylic Fluorination of Aza‐Heterocycles Induced by Single‐Electron Transfer to Selectfluor
Author(s) -
Danahy Kelley E.,
Cooper Julian C.,
Van Humbeck Jeffrey F.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201801280
Subject(s) - selectfluor , intermolecular force , chemistry , electrophile , selectivity , electrophilic fluorination , dissociation (chemistry) , electron transfer , halogenation , bond dissociation energy , reagent , computational chemistry , combinatorial chemistry , organic chemistry , photochemistry , molecule , catalysis
A selective and mild method for the benzylic fluorination of aromatic azaheterocycles with Selectfluor is described. These reactions take place by a previously unreported mechanism, in which electron transfer from the heterocyclic substrate to the electrophilic fluorinating agent Selectfluor eventually yields a benzylic radical, thus leading to the desired C−F bond formation. This mechanism enables high intra‐ and intermolecular selectivity for aza‐heterocycles over other benzylic components with similar C−H bond‐dissociation energies.