50446-43-0Relevant academic research and scientific papers
Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: Formal [2+2+1] synthesis of pyrroles
Pearce, Adam J.,See, Xin Yi,Tonks, Ian A.
, p. 6891 - 6894 (2018/06/26)
Catalytic oxidative nitrene transfer from azides with the early transition metals is rare, and has not been observed without the support of redox noninnocent spectator ligands. Here, we report the formal [2+2+1] coupling of azides and alkynes via TiII/TiIV redox catalysis from simple Ti halide imido precatalysts. These reactions yield polysubstituted N-alkyl pyrroles, including N-benzyl protected pyrroles and rare examples of very electron rich pentaalkyl pyrroles. Mechanistic analysis reveals that [2+2+1] reactions with bulky azides have different mechanistic features from previously-reported reactions using azobenzene as a nitrene source.
A ruthenium-based catalytic system with switchable selectivity between cyclotrimerization and enyne metathesis/Diels-Alder reactions of terminal alkynes
Karabulut, Solmaz,Sariaslan, Begüm,?ztürk, Bengi ?zgün
, p. 12 - 16 (2013/08/23)
In this study, we report a practical catalytic system, [RuCl 2(p-cymene)]2/IPr (IPr: 1,3-bis(2,6 diisopropylphenyl) imidazol-2-ylidene), that can switch between cyclotrimerization and cross enyne metathesis. The cyclotrimerization reaction of phenylacetylene catalyzed by [RuCl2(p-cymene)]2 can be switched to enyne metathesis by the introduction of a sterically hindered N-heterocyclic carbene. The 1,3-diene formed during this reaction reacts with dienophiles to form the Diels-Alder adduct. A practical one-pot synthesis method, utilizing enyne metathesis/Diels-Alder reactions, was used to construct cyclic compounds in an efficient manner.
Zirconocene bis(perfluorooctanesulfonate) s-catalyzed highly efficient synthesis of 1,3,5-triaryl benzene via cyclotrimerization of ketones
Zhang, Guo Ping,Qiu, Ren Hua,Xu, Xin Hua,Zhou, Hai Hui,Kuang, Ya Fei,Chen, Si Hai
experimental part, p. 858 - 864 (2012/01/19)
Air-stable zirconocene bis(perfluoroctanesulfonate) s [Cp 2Zr]OSO2C8F17) 2] (1) with high Lewis acidity and high thermal stability was prepared by the reaction between Cp2ZrCl2 a
The highly selective formation of biaryls by the cyclization of arylethynes catalyzed by vanadyl phthalocyanine
Cicero, Daniel,Lembo, Angelo,Leoni, Alessandro,Tagliatesta, Pietro
experimental part, p. 2162 - 2165 (2009/12/25)
The dimerization of arylethynes catalyzed by vanadium phthalocyanine to give substituted biaryls has been investigated. The reaction yield is always high and for many examples is only slightly affected by the aryl substituents. This fact is also related to the results obtained with metalloporphyrins, which give lower selectivities due to the presence of variable amounts of triphenylbenzenes.
Increased conversion to 2,4,6-triarylpyrylium salt: Aldol cyclotrimerization of acetophenone in BMImPF6 ionic liquid
Chuang, Po-Neng,Wu, Tsao-Dong,Liu, Ling-Kang
experimental part, p. 512 - 516 (2009/05/11)
Substituted acetophenone 1 in BMImPF6 ionic liquid, heated at 120 °C for 24 h, produces β-methylchalcone 2, triarylbenzene 3, and triarylpyrylium salt 4. BMImPF6 catalyzes the self-aldol condensation of 1, whose cyclotrimerization gi
Unusual Products from the Reactions of Anhydrous Hydrogen Chloride with Arylacetylenes
Griesbaum, Karl,Rao, V. V. Ramana,Leifker, Gregor
, p. 4975 - 4981 (2007/10/02)
Liquid-phase reactions of anhydrous hydrogen chloride with p-methyl-, p-methoxy-, p-fluoro-, and unsubstituted phenylacetylene afforded cyclic trimers, tetramers, and pentamers of the corresponding arylacetylenes.Phenylacetylene gave additionally 1-methyl-1-phenyl-3-chloroindene.The reactions proceeded via the corresponding HCl diadducts, i.e., via 1-aryl-1,1-dichloroethanes as intermediates.
