24004-64-6Relevant 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)
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
Bicyclic lactones
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, (2008/06/13)
Process for preparing bicyclic lactone acrylic aldehydes and ketones of the formula STR1 wherein "n" is one or 2, wherein R1, is hydrogen, methyl, or ethyl, and wherein R4 is hydrogen or a blocking group; and those aldehydes, ketones, and intermediates prepared therein. The aldehydes and ketones are useful intermediates in preparing prostaglandins and analogs having pharmacological utility.
