84307-76-6

Upstream product

• 54125-02-9 danishefsky's diene 
• 538-51-2 benzylidene phenylamine 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 66955-68-8 (RS)-(+/-)-6-Methylthio-1,2-diphenyl-2,3-dihydropyridin-4(1H)-one 
• 1423-60-5 methyl ethynyl ketone 
• 444879-08-7 6-methoxy-1,2-diphenyl-4-trimethylsilanyloxy-1,2,3,6-tetrahydro-pyridine 
• 98-95-3 nitrobenzene 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 174653-09-9 (RS)-(+/-)-N,N-Dimethyl-2-phenyl-6-phenylimino-3,6-dihydro-2H-thiopyran-4-amine 
• 174653-12-4 (RS)-(+/-)-4-Dimethylamino-1,6-diphenyl-5,6-dihydropyridine-2(1H)-thione 
• 33993-35-0 cis-benzylideneaniline 

Relevant academic research and scientific papers

Lithium heptadecafluorooctanesulfonate catalyzed Mannich-type and aza-Diels-Alder reactions in supercritical carbon dioxide

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

Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media

Three-component aza Diels-Alder reaction, starting from aldehyde, aniline, and Danishefsky's diene, took place smoothly under the influence of HBF4 in aqueous media to afford dihydro-4-pyridone derivatives in high yields.

Hydrogen-Bonding Catalysis of Tetraalkylammonium Salts in an Aza-Diels–Alder Reaction

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.

Aza-Diels-Alder reaction catalyzed by perfluorinated metal salts in fluorous phase

In this paper, we describe the aza-Diels-Alder reaction of Danishefsky's diene with arylaldehydes and aromatic amines in a fluorous phase. With perfluorodecalin (C10F18, cis- and transmixture) as the fluorous solvent and a perfluorin

[(PPh3)Ag(CB11H6Y6)] (Y = H, Br): Highly active, selective and recyclable Lewis acids for a hetero-Diels-Alder reaction

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

Chiral Ferrocenyl?Iodotriazoles and ?Iodotriazoliums as Halogen Bond Donors. Synthesis, Solid State Analysis and Catalytic Properties.

Despite the increasing number of applications based on halogen bond (XB), asymmetric catalysis purely based on such supramolecular interactions still remains a huge challenge. The first step toward its development is the design of appropriate XB chiral donor molecules with good catalytic properties. In this context, we report the synthesis of a series of iodinated compounds based on the triazole or triazolium ring and possessing the planar chirality of ferrocene. Their XB donor property was attested by X-ray diffraction analysis, showing short I???N and I???F interactions in the triazole-based derivatives and in the tetrafluoroborate salt of a idodotriazolium, respectively. The potential of these compounds to act as XB-based catalysts was demonstrated in the aza-Diels-Alder reaction involving an imine and a diene. Whereas triazole-based derivatives were inactive in this reaction, the triflate salts of iodotriazoliums delivered the expected cycloadduct with high yield.

Insight into the Modes of Activation of Pyridinium and Bipyridinium Salts in Non-Covalent Organocatalysis

A series of pyridinium and bipyridinium salts were prepared and their catalytic properties were evaluated in the aza-Diels-Alder reaction between imines and Danishefsky diene. Depending on the substituents of the pyridinium/bipyridinium rings and on the nature of the counterion, two mechanisms of activation were demonstrated. In case of non-substituted rings, the substrate is activated through charge transfer involving the aryl ring on the C-side of the imine. When halogen atoms were introduced on the catalysts, the activation mode switched to halogen bond involving the imine nitrogen lone pair. Moreover, alternative activation modes based on hydrogen bonding and radical cation were ruled out. This work allowed us to develop two families of catalysts whose potential was demonstrated in the cycloaddition of various imines with Danishefsky diene. The first family is composed of the simple methyl pyridinium triflate and dioctyl bipyridinium triflate. The former is active only with imines bearing a p-methoxyphenyl group on the C-side and the latter was found to be efficient with imines bearing different substituents on both the N- and C-sides of the imines. The second family is based on halogenated pyridinium salts which proved active with almost all considered imines. (Figure presented.).

Chalcogen-Bonding Catalysis with Telluronium Cations

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.

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

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.

Trialkylsulfonium and tetraalkylammonium salts as hydrogen-bonding catalysts in an aza-diels-alder reaction: Experimental and computational studies

Hydrogen-bonding catalysis by cyclic trialkylsulfonium and tetraalkylammonium salts in an aza-Diels-Alder reaction was investigated. Among the examined onium salt catalysts, cyclic trialkylsulfonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate possessing a non-coordinating counter anion was the most effective. Details of the activation modes of cyclic trialkylsulfonium and tetraalkylammonium salts were discussed on the basis of DFT calculation.