77935-95-6Relevant academic research and scientific papers
Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base
Zhao, Na,Lin, Chengdong,Wen, Lirong,Li, Zhibo
, p. 3432 - 3440 (2019/05/15)
Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre
Substrate-Controlled Regio- and Stereoselective Synthesis of (Z)- and (E)- N-Styrylated Carbazoles, Aza-carbazoles, and γ-Carbolines via Hydroamination of Alkynes
Garg, Vineeta,Kumar, Pradeep,Verma, Akhilesh K.
, p. 11686 - 11702 (2018/09/21)
We report herein the substrate-controlled regio- and stereoselective hydroamination of carbazoles, aza-carbazoles, and γ-carbolines with functionalized aromatic as well as aliphatic alkynes in a KOH/DMSO system in good yields. The electronic effect of the substrates governs the stereochemistry of the product. Electron-donating alkynes provided (Z)-stereoselective products, and electron-withdrawing alkynes provided (E)-stereoselective products. This approach also provides an easy route for the synthesis of mono- and bis-hydroaminated product. The deuterium-labeling studies were also conducted to support the mechanistic pathway.
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.
A general copper-catalyzed coupling of azoles with vinyl bromides
Liao, Qian,Wang, Yuxing,Zhang, Liyun,Xi, Chanjuan
supporting information; experimental part, p. 6371 - 6373 (2009/12/08)
(Chemical Equation Presented) A copper-catalyzed methodology for the coupling of vinyl bromides with azoles has been developed. This protocol uses a combination of 10 mol % of copper iodide and 20 mol % of ethylenediamine as catalyst. The reaction proceed
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
9-ALKENYLCARBAZOLES. 7. REGIOSPECIFIC AND STEREOSPECIFIC ADDITION OF CARBAZOLE AND INDOLE TO PHENYLACETYLENE. STRUCTURE AND SOME PROPERTIES OF cis-9-(2-PHENYLVINYL)CARBAZOLE
Filimonov, V. D.
, p. 148 - 151 (2007/10/02)
Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole.A cis-phenyl group merkedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom.It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays ?-donor properties with respect to the styryl group.
