7528-45-2Relevant academic research and scientific papers
Zinc-Catalyzed Dehydrogenative Silylation of Indoles
Yonekura, Kyohei,Iketani, Yoshihiko,Sekine, Masaru,Tani, Tomohiro,Matsui, Fumiya,Kamakura, Daiki,Tsuchimoto, Teruhisa
, p. 3234 - 3249 (2017/09/18)
A unique Lewis acid/base system consisting of zinc triflate and pyridine was found to act as an effective catalyst for making an N(indolyl)-Si bond in a dehydrogenative fashion. Execution in a nitrile medium brings out the best performance of the Zn-pyridine system, which enables participation of flexible pieces of indoles and hydrosilanes, thereby giving diverse N-silylindoles in high to excellent yields. The Zn-pyridine system in the nitrile solvent is also applicable to the corresponding C-silylation in the case that the nitrogen atom of indoles has a substituent. Pyrrole, carbazole, arylamine, and thiophene substrates other than indoles undergo the dehydrogenative N- and/or C-silylation as well. Mechanistic studies showed that the role of the zinc Lewis acid is to activate the hydrosilane. The rate-determining step of the present reaction was found to be involved in the stage of the indolyl-H bond cleavage, on the basis of kinetic isotope effect experiments. Kinetic studies indicated that the indole-based dehydrogenative N-silylation is first-order in indole, second-order in each of hydrosilane and zinc triflate, and positive and negative fractional orders in pyridine.
Catalytic metal-free Si-N cross-dehydrocoupling
Greb, Lutz,Tamke, Sergej,Paradies, Jan
supporting information, p. 2318 - 2320 (2014/03/21)
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 cou
