Catalytic metal-free Si-N cross-dehydrocoupling.
The metal-free B(C6F5)3 catalyzed dehydrocoupling of hydrosilanes with anilines, carbazoles and indoles is reported. For anilines and carbazoles the reaction proceeds by the liberation of H2 as the sole Si-N coupling byproduct. Indoles react with diphenyl(methyl) hydrosilane to give N-silyl indolines with high diastereoselectivity (d.r. 10 : 1) in excellent yields. A mechanism for this Si-N coupling/hydrogenation sequence is proposed.
Institute for Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany. jan.paradies@kit.edu.
Lutz
L
Greb
Sergej
S
Tamke
Jan
J
Paradies