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Transition‐Metal‐Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
Author(s) -
Finck Lucie,
Oestreich Martin
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.202101731
Subject(s) - nucleophile , aryl , chemistry , fluoride , nucleophilic aromatic substitution , catalysis , combinatorial chemistry , transition metal , surface modification , coupling (piping) , photochemistry , medicinal chemistry , nucleophilic substitution , organic chemistry , inorganic chemistry , materials science , alkyl , metallurgy
A chemoselective C(sp 2 )−C(sp 2 ) coupling of sufficiently electron‐deficient fluorinated arenes and functionalized N ‐aryl‐ N’ ‐silyldiazenes as masked aryl nucleophiles is reported. The fluoride‐promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (S N Ar). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.