title: Friedel-Crafts-Type Intermolecular C-H Silylation of Electron-Rich Arenes Initiated by Base-Metal Salts.
abstract: An electrophilic aromatic substitution (SE 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 SE Ar of electron-rich arenes with hydrosilanes but not halosilanes. This new C-H silylation was optimized for FeCl2/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.
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.
authors.forename: Qin
authors.initials: Q
authors.lastname: Yin
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.
authors.forename: Hendrik F T
authors.identifier: http://orcid.org/0000-0003-3748-6609
authors.initials: HF
authors.lastname: Klare
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany. martin.oestreich@tu-berlin.de.
authors.forename: Martin
authors.identifier: http://orcid.org/0000-0002-1487-9218
authors.initials: M
authors.lastname: Oestreich
keywords: C−H activation; Lewis acids; Si−H activation; electrophilic substitution; hydrosilanes