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Copper‐Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride
Author(s) -
Dorel Ruth,
Boehm Philip,
Schwinger Daniel P.,
Hartwig John F.
Publication year - 2020
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.201905040
Subject(s) - nucleophile , steric effects , aryl , regioselectivity , fluoride , chemistry , silylation , copper , functional group , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , alkyl , polymer
A method for the nucleophilic fluorination of heptamethyl aryl trisiloxanes to form fluoroarenes is reported. The reaction proceeds in the presence of Cu(OTf) 2 and KHF 2 as the fluoride source under mild conditions for a broad range of heptamethyltrisiloxyarenes with high functional group tolerance. The combination of this method with the silylation of aryl C−H bonds enables the regioselective fluorination of non‐activated arenes controlled by steric effects following a two‐step protocol.