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Friedel–Crafts‐Type Intermolecular C−H Silylation of Electron‐Rich Arenes Initiated by Base‐Metal Salts
Author(s) -
Yin Qin,
Klare Hendrik F. T.,
Oestreich Martin
Publication year - 2016
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.201510469
Subject(s) - silylation , intermolecular force , friedel–crafts reaction , base (topology) , chemistry , metal , electron , type (biology) , medicinal chemistry , polymer chemistry , organic chemistry , molecule , catalysis , mathematics , physics , geology , mathematical analysis , paleontology , quantum mechanics
An electrophilic aromatic substitution (S E Ar) with a catalytically generated silicon electrophile is reported. Essentially any commercially available base‐metal salt acts as an initiator/catalyst when activated with NaBAr F 4 . The thus‐generated Lewis acid then promotes the S E Ar of electron‐rich arenes with hydrosilanes but not halosilanes. This new C−H silylation was optimized for FeCl 2 /NaBAr F 4 , affording good yields at catalyst loadings as low as 0.5 mol %. The procedure is exceedingly straightforward and comes close to typical Friedel–Crafts methods, where no added base is needed to absorb the released protons.