95249-64-2Relevant academic research and scientific papers
Ethanol as a Hydrogenating Agent: Palladium-Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides
Siva Reddy, Alla,Kumara Swamy
supporting information, p. 6984 - 6988 (2017/06/06)
Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source gives Z enamides. The role of ethanol in hydrogenation was demonstrated by means deuterium labeling experiment.
Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines
Tahara, Atsushi,Miyamoto, Yasumitsu,Aoto, Ryuta,Shigeta, Keisuke,Une, Yuta,Sunada, Yusuke,Motoyama, Yukihiro,Nagashima, Hideo
, p. 4895 - 4907 (2015/11/09)
The appropriate design of a ligand (L) in IrCl(CO)(L)2 (4) realized the efficient synthesis of π-conjugated enamines possessing hole-transport properties. The iridium complex with electron-withdrawing phosphorus ligands catalyzed the hydrosilylation of amides to the corresponding silylhemiaminals, which were transformed to the enamines by heat or by treatment with acids. High catalytic efficiency (TON > 10,000) was achieved, which made it possible for the residual iridium in the enamine product to be below 20 ppb.
Highly stereoselective synthesis, structure, and application of (E)-9-[2-(Silyl)ethenyl]-9H-carbazoles
Marciniec, Bogdan,Majchrzak, Mariusz,Prukala, Wieslaw,Kubicki, Maciej,Chadyniak, Dariusz
, p. 8550 - 8555 (2007/10/03)
(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)-AT-(phenylvinyl)-carbazole with high yield and stereoselectivity.
Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine
Lebedev, Artyom Y.,Izmer, Vyatcheslav V.,Kazyul'kin, Denis N.,Beletskaya, Irina P.,Voskoboynikov, Alexander Z.
, p. 623 - 626 (2007/10/03)
(formula presented) Vinylation of various azoles (pyrrole, indole, carbazole, and their derivatives) and phenothiazine with vinyl bromides catalyzed by palladium-phosphine complexes results in the respective N-vinylazoles in 30-99% yields. This reaction w
A new route to N-substituted heterocycles
Katritzky, Alan R.,Lang, Hengyuan,Lan, Xiangfu
, p. 2829 - 2838 (2007/10/02)
N-(Benzotriazol-1-ylmethyl)-indole, - pyrrole, -carbazole, and -benzimidazole, and analogs substituted in the methylene group are converted by lithium aluminum hydride, or by Grignard reagents, or in two cases by organozinc reagents, into the N-substituted heterocycles in good yields.
α-Lithiation of N-Alkylcarbazoles: Preparation of N-(E)-Styrylcarbazole
Katritzky, Alan R.,Saczewski, Franciszek,Marson, Charles M.
, p. 1351 - 1355 (2007/10/02)
Alkylation of carbazole with benzene gave the key intermediate N-carbazole (2).Treatment of 2 with n-butyllithium at low temperature gave an α-lithio derivative 3, which reacted with a variety of electrophiles, affording N-carbazoles 4a-g.Removal of the activating phenylthio group in 4a-g was achieved by Raney nickel desulfurization.Three successful routes to the novel N-(E)-styrylcarbazole (10) are described. 1H NMR and 13C NMR assignments of N-alkylcarbazoles are discussed.
