84307-76-6Relevant articles and documents
Lithium heptadecafluorooctanesulfonate catalyzed Mannich-type and aza-Diels-Alder reactions in supercritical carbon dioxide
Shi, Min,Cui, Shi-Cong,Li, Qing-Jiang
, p. 6163 - 6167 (2004)
The Mannich-type reaction of imines with (1-methoxy-2-methylpropenyloxy) trimethylsilane and aza-Diels-Alder reaction of imines with Danishefsky's diene can be carried out in scCO2 in the presence of lithium heptadecafluorooctanesulfonate which
Hydrogen-Bonding Catalysis of Tetraalkylammonium Salts in an Aza-Diels–Alder Reaction
Kumatabara, Yusuke,Kaneko, Shiho,Nakata, Satoshi,Shirakawa, Seiji,Maruoka, Keiji
, p. 2126 - 2129 (2016)
A piperidine-derived tetraalkylammonium salt with a non-coordinating counteranion worked as an effective hydrogen-bonding catalyst in an aza-Diels–Alder reaction of imines and a Danishefsky diene. The hydrogen-bonding interaction between the ammonium salt and an imine was observed as part of a 1H NMR titration study.
[(PPh3)Ag(CB11H6Y6)] (Y = H, Br): Highly active, selective and recyclable Lewis acids for a hetero-Diels-Alder reaction
Hague,Patmore,Frost,Mahon,Weller
, p. 2286 - 2287 (2001)
The complex [(PPh3)Ag(CB11H6Br6)] 1 is an effective and selective catalyst (0.1 mol% loading) for a hetero-Diels-Alder reaction, which shows a marked dependence on the presence of trace amounts of water, while a
Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis
He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung
, p. 12632 - 12642 (2021/10/21)
Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.
Chalcogen-Bonding Catalysis with Telluronium Cations
Aubert, Emmanuel,Mamane, Victor,Pale, Patrick,Weiss, Robin
supporting information, p. 19281 - 19286 (2021/07/25)
Chalcogen bonding results from non-covalent interactions occurring between electrodeficient chalcogen atoms and Lewis bases. Among the chalcogens, tellurium is the strongest Lewis acid, but Te-based compounds are scarcely used as organocatalysts. For the first time, telluronium cations demonstrated impressive catalytic properties at low loadings in three benchmark reactions: the Friedel–Crafts bromination of anisole, the bromolactonization of ω-unsaturated carboxylic acids and the aza-Diels–Alder between Danishefsky's diene and imines. The ability of telluronium cations to interact with a Lewis base through chalcogen bonding was demonstrated on the basis of multi-nuclear (17O, 31P, and 125Te) NMR analysis and DFT calculations.