Highly stereoselective synthesis, structure, and application of (E)-9-[2-(silyl)ethenyl]-9H-carbazoles.
(E)-N-(Silyl)vinylcarbazole has been easily prepared via a new catalytic route, silylative coupling (SC) of vinylcarbazole with vinyltrisubstituted silanes catalyzed by [RuH(Cl)(CO)(PCy3)2]. X-ray structures of two silylvinylcarbazoles as first N-vinylcarbazole derivatives have been resolved. The Pd-catalyzed Hiyama coupling reaction (also as the tandem reaction with SC) of synthesized (E)-N-(triethoxysilyl)vinylcarbazole with iodobenzene has been performed to afford (E)-N-(phenylvinyl)carbazole with high yield and stereoselectivity.
Marciniec
Bogdan
B
Department of Organometallic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland. marcinb@amu.edu.pl
Majchrzak
Mariusz
M
Prukała
Wiesław
W
Kubicki
Maciej
M
Chadyniak
Dariusz
D