869938-32-9Relevant academic research and scientific papers
Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions
Kudale, Vishal Suresh,Li, Jing,Mutra, Mohana Reddy,Tsai, Wu-Hsun,Wang, Jeh-Jeng
supporting information, p. 2288 - 2300 (2020/04/21)
Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.
Synthesis of Chlorotrifluoromethylated Pyrrolidines by Electrocatalytic Radical Ene-Yne Cyclization
Ye, Ke-Yin,Song, Zhidong,Sauer, Gregory S.,Harenberg, Johannes H.,Fu, Niankai,Lin, Song
, p. 12274 - 12279 (2018/08/31)
The stereoselective synthesis of chlorotrifluoromethylated pyrrolidines was achieved using anodically coupled electrolysis, an electrochemical process that combines two parallel oxidative events in a convergent and productive manner. The bench-stable and
Benzimidazolium- and Benzimidazolilydene-Capped Cyclodextrins: New Perspectives in Anion Encapsulation and Gold-Catalyzed Cycloisomerization of 1,6-Enynes
Kaya, Zeyneb,Andna, Lucile,Matt, Dominique,Bentouhami, Embarek,Djukic, Jean-Pierre,Armspach, Dominique
, p. 17921 - 17926 (2018/11/23)
A new way of introducing a N-heterocyclic carbene cap onto cyclodextrins has been devised. The benzimidazolium intermediates were found to behave as receptors towards cavity matching anions. The corresponding C1- and C2-symmetrical r
Copper-Catalyzed [2 + 2 + 3] Annulation of 1,6-Enynes with α-Bromo-1,3-Dicarbonyl Compounds: Synthesis of Dihydrooxepines
Zheng, Lan,Liang, Yong-Min
, p. 7000 - 7007 (2017/07/15)
Copper-catalyzed [2 + 2 + 3] annulation of 1,6-enynes with α-bromo-1,3-dicarbonyl compounds is described. This reaction provides facile access to seven-membered dihydrooxepines for epidithiodiketopiperazines with two newly formed C-C bonds and one C-O bon
Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: Facile synthesis of bicyclo[4.1.0]heptan-5-ones
Liu, Bang,Song, Ren-Jie,Ouyang, Xuan-Hui,Li, Yang,Hu, Ming,Li, Jin-Heng
, p. 12819 - 12822 (2015/08/06)
We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cycl
Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate
Wang, Yu-Qi,He, Yu-Tao,Zhang, Lu-Lu,Wu, Xin-Xing,Liu, Xue-Yuan,Liang, Yong-Min
, p. 4280 - 4283 (2015/09/15)
A novel and convenient Pd-catalyzed radical cascade iododifluoromethylation/cyclization of 1,6-enynes with ethyl difluoroiodoacetate is demonstrated. The proposed transformation presents high stereoselectivity under mild and facile reaction conditions, th
Copper-Catalyzed Cascade Cyclization for the Synthesis of Trifluoromethyl-Substituted Spiro-2H-azirines from 1,6-Enynes
He, Yu-Tao,Wang, Qiang,Zhao, Jiahui,Wang, Xiao-Zhen,Qiu, Yi-Feng,Yang, Yu-Chen,Hu, Jing-Yuan,Liu, Xue-Yuan,Liang, Yong-Min
, p. 3069 - 3075 (2015/11/03)
A method for the synthesis of trifluoromethyl CF3-substituted spirocyclic compounds containing with a unique quaternary carbon center from readily available starting materials has been developed. The reaction provides a facile access to 2H-azir
Copper-catalyzed three-component cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes
He, Yu-Tao,Li, Lian-Hua,Zhou, Zhao-Zhao,Hua, Hui-Liang,Qiu, Yi-Feng,Liu, Xue-Yuan,Liang, Yong-Min
, p. 3896 - 3899 (2014/08/18)
A novel three-component strategy for the cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid a
Lewis acid mediated intramolecular C-C bond formation of alkyne-epoxide leading to six-membered nitrogen and oxygen heterocycles
Ghosh, Priya,Saha, Pipas,Bondalapati, Somasekhar,Indukuri, Kiran,Saikia, Anil K.
, p. 4119 - 4124 (2014/05/20)
Intramolecular C-C bond formation of oxygen- and nitrogen-tethered alkynes and epoxide mediated by Lewis acid under ambient conditions is described. A simple procedure for the synthesis of 3,6- and 5,6-dihydropyrans and 3,4-dehydropiperidines from acyclic
Copper-catalyzed trifluoromethylation-cyclization of enynes: Highly regioselective construction of trifluoromethylated carbocycles and heterocycles
Gao, Pin,Yan, Xiao-Biao,Tao, Tao,Yang, Fan,He, Ting,Song, Xian-Rong,Liu, Xue-Yuan,Liang, Yong-Min
, p. 14420 - 14424 (2013/11/06)
Regioselective trifluoromethylation-cyclization: A method for copper-catalyzed trifluoromethylation-cyclization of simple enynes using the C-C triple bond as a nucleophile is reported for the first time (see scheme). The reaction proceeds efficiently in a
