title: A Catalytic SE Ar Approach to Dibenzosiloles Functionalized at Both Benzene Cores.
abstract: A general procedure for the catalytic preparation of dibenzosiloles functionalized at one or both benzene rings starting from readily available ortho-silylated biphenyls is reported. This method provides rapid access to silole building blocks substituted with chlorine atoms at both phenylene groups, thereby allowing catalytic access to directly polymerizable dibenzosiloles. Moreover, it is shown that, despite the involvement of highly electrophilic intermediates, a considerable range of Lewis-basic, for example, oxygen- and nitrogen-containing, functional groups is tolerated. The mechanism of this intramolecular electrophilic aromatic substitution (SE Ar) proceeds through a sulfur-stabilized silicon cation, generated catalytically from the hydrosilane precursor.
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de.
authors.forename: Lukas
authors.initials: L
authors.lastname: Omann
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de. martin.oestreich@tu-berlin.de.
authors.forename: Martin
authors.initials: M
authors.lastname: Oestreich
keywords: SiH bond activation; electrophilic substitution; homogeneous catalysis; microwave chemistry; regioselectivity