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meta ‐Selective C−H Arylation of Fluoroarenes and Simple Arenes
Author(s) -
Liu LuoYan,
Qiao Jennifer X.,
Yeung KapSun,
Ewing William R.,
Yu JinQuan
Publication year - 2020
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.202002865
Subject(s) - chemistry , selectivity , metalation , reactivity (psychology) , protonation , catalysis , yield (engineering) , benzene , deuterium , norbornene , ligand (biochemistry) , medicinal chemistry , photochemistry , organic chemistry , ion , receptor , copolymer , medicine , materials science , alternative medicine , physics , pathology , quantum mechanics , metallurgy , biochemistry , polymer
Fluorine is known to promote ortho ‐C−H metalation. Based upon this reactivity, we employed an activated norbornene that traps the ortho ‐palladation intermediate and is then relayed to the meta position, leading to meta ‐selective C−H arylation of fluoroarenes. Deuterium experiment suggests that this meta ‐arylation is initiated by ortho C−H activation and the catalytic cycle is terminated by C‐2 protonation. A dual‐ligand system is crucial for the observed high reactivity and site selectivity. Applying this approach to simple benzene or other arenes also affords arylation products with good yield and site selectivity.