Brønsted Acid-Promoted Formation of Stabilized Silylium Ions for Catalytic Friedel-Crafts C-H Silylation.
A counterintuitive approach to electrophilic aromatic substitution with silicon electrophiles is disclosed. A strong Brønsted acid that would usually promote the reverse reaction, i.e., protodesilylation, was found to initiate the C-H silylation of electron-rich (hetero)arenes with hydrosilanes. Protonation of the hydrosilane followed by liberation of dihydrogen is key to success, fulfilling two purposes: to generate the stabilized silylium ion and to remove the proton released from the Wheland intermediate.
Institut für Chemie, Technische Universität Berlin , Strasse des 17. Juni 115, 10623 Berlin, Germany.
Qing-An
QA
Chen
Institut für Chemie, Technische Universität Berlin , Strasse des 17. Juni 115, 10623 Berlin, Germany.
Hendrik F T
HF
Klare
Institut für Chemie, Technische Universität Berlin , Strasse des 17. Juni 115, 10623 Berlin, Germany.
Martin
M
Oestreich