940965-20-8Relevant academic research and scientific papers
Rh(II)-Catalyzed Chemoselective Oxidative Amination and Nucleophilic Trapping of gem-Dimethyl Alkynyl-Tethered Sulfamates
Pan, Dong,Wei, Yin,Shi, Min
supporting information, p. 84 - 87 (2018/01/17)
A Rh(II)-catalyzed chemoselective oxidative amination and nucleophilic trapping of gem-dimethyl sulfamates has been presented. For 2,2-dimethyl-4-arylbut-3-yn-1-yl sulfamates, the reactions underwent a metallonitrene-initiated alkyne oxidation along with nucleophilic trapping of H2O upon oxidation, giving aroyl group containing heterocycles. For 2,2-dimethyl-4-arylpent-3-yn-1-yl sulfamates, the α-iminometal carbene intermediate was trapped by aryl group migration, delivering a styryl group containing heterocycles.
Csp-Csp3 Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes
Shen, Yangyong,Huang, Bo,Zheng, Jing,Lin, Chen,Liu, Yu,Cui, Sunliang
, p. 1744 - 1747 (2017/04/11)
An iron(III)-promoted hydroalkynylation of unactivated alkenes toward Csp-Csp3 bond formation has been developed. Various alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified alkynes in this chemoselective protocol. Additionally, the scalability was unraveled and the further divergent transformations of products were conducted to demonstrate the synthetic utility.
The mechanism of gold(I)-catalyzed hydroalkoxylation of alkynes: An extensive experimental study
Zhdanko, Alexander,Maier, Martin E.
supporting information, p. 1918 - 1930 (2014/03/21)
An extensive experimental study of the mechanism of gold(I)-catalyzed hydroalkoxylation of internal alkynes has been conducted by using NMR spectroscopy. This study was focused on the organogold intermediates, observations of actual catalytic intermediates in situ, and the reaction kinetics that are involved in this reaction. Based on the experimental results, a complete mechanistic picture was established, including on- and off-cycle processes that explain the role of diaurated species. We have shown that gold-catalyzed hydroalkoxylation of internal alkynes is a reaction that requires only one gold atom for the catalytic cycle, disproving a recent hypothesis regarding the involvement of cooperative gold catalysis.
Catalyst-dependent divergent synthesis of pyrroles from 3-alkynyl imine derivatives: A noncarbonylative and carbonylative approach
Chen, Gen-Qiang,Zhang, Xiao-Nan,Wei, Yin,Tang, Xiang-Ying,Shi, Min
, p. 8492 - 8497 (2014/08/18)
A novel Ru0- and RhI-catalyzed noncarbonylative and carbonylative cycloisomerization of readily available 3-alkynyl imine derivatives has been developed to provide 3,4-fused or nonfused pyrrole derivatives efficiently in moderate to
Gold-catalyzed hydrative carbocyclization of 1,5- and 1,6-diyn-3-ones via an oxygen transfer process
Tang, Jhih-Meng,Liu, Ting-An,Liu, Rai-Shung
supporting information; experimental part, p. 8479 - 8483 (2009/04/04)
(Chemical Equation Presented) This study reports new hydrative carbocyclizations of 1,5- and 1,6-diyn-3-ones catalyzed by PPh3AuOTf, involving a π-alkyne-assisted oxygen transfer in the reaction mechanisms. Treatment of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes with PPh3AuOTf (5 mol %) in wet 1,4-dioxane (23°C, 10 min) led to hydrative aromatization to give 4-hydroxyl-1-naphthyl ketones efficiently. This approach is also extendible to the hydrative cyclization of acyclic 1,5-diyn-3-ones, which afforded 4-cyclopentenonyl ketones in reasonable yields. On the basis of this oxygen-labeling study, we propose a plausible mechanism involving an alkyne-assisted oxygen transfer to generate key oxonium and gold-enolate intermediates.
The Ring Opening of Unsymmetrical Allylic, Benzylic, Propargylic, and Si-Substituted Epoxides by Titanium Acetylides: A Convenient Access to Certain 2-Substituted 3-Butyn-1-ols
Krause, Norbert,Seebach, Dieter
, p. 1315 - 1320 (2007/10/02)
Epoxides bearing aryl, alkenyl, alkynyl, and trimethylsilyl substituents react with titanium acetylides at the higher substituted carbon atom exclusively; the 2-substituted 3-butyn-1-ols thus formed are isolated in 33-79percent yield.The dependence of the yield on the solvent, the ratio of the reactands, and their structure is discussed and a reaction mechanism is proposed.
