106947-61-9Relevant academic research and scientific papers
First palladium-catalyzed aminations of aryl chlorides
Beller, Matthias,Riermeier, Thomas H.,Reisinger, Claus-Peter,Herrmann, Wolfgang A.
, p. 2073 - 2074 (1997)
The palladium-catalyzed coupling reaction of aryl chlorides with various amines has been studied for the first time. Crucial for the success of this C-N bond forming reaction is the use of potassium tert-butoxide as base. Turn over numbers up to 900 and y
One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy
De Jong, Jorn,Heijnen, Dorus,Helbert, Hugo,Feringa, Ben L.
supporting information, p. 2908 - 2911 (2019/03/17)
A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.
α-Cyanation of Aromatic Tertiary Amines using Ferricyanide as a Non-Toxic Cyanide Source
Nauth, Alexander M.,Otto, Nicola,Opatz, Till
supporting information, p. 3424 - 3428 (2016/01/25)
The reaction of aromatic tertiary amines with potassium ferricyanide directly provides the useful α-amino nitriles. The inexpensive iron complex functions both as an oxidant and as a cyanide source. The presence of molecular oxygen speeds up the reaction which can be performed in aqueous tert-butanol or even in ethanol-based mixtures like Tequila. While amine cyanations usually employ highly toxic cyanide sources, potassium ferricyanide is even less toxic than table salt. No expensive metal complexes are required as catalysts and the co-product of the cyanation, Prussian blue, has no known toxicity and is rather used as an antidote.
Amination of electron deficient aryl chlorides promoted by nano sized Mg(OH)2 under transition metals free condition
Cui, Zhi Hao,Meng, Zi Hui,Mi, Yan Qing,Wang, Peng,Wang, Qi,Zhao, Lin Man,Cui, Ke Jian,Yu, Fang,Xu, Zhi Bin
experimental part, p. 137 - 140 (2012/06/18)
This paper presents the amination reactions of electron deficient aryl chlorides promoted by Mg(OH)2 without transition metals. Only using stoichiometric amount of nano sized Mg(OH)2, good to moderate isolated yields could be achieved in N-methylpyrrolidone (NMP) after 24 h at 150 °C.
An efficient silane-promoted nickel-catalyzed amination of aryl and heteroaryl chlorides
Manolikakes, Georg,Gavryushin, Andrei,Knochel, Paul
, p. 1429 - 1434 (2008/04/05)
(Chemical Equation Presented) A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)2, 1 mol % of 3,5,6,8-tetrabromo-1,10-phenanthroline, and polymethylhydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.
The effects of cyclic terminal groups in di- and tri-arylmethane dyes. Part 3. Consequences of unsymmetrical substitution in Malachite Green
Gorman, Stephen A.,Hepworth, John D.,Mason, Donald
, p. 1889 - 1895 (2007/10/03)
A comprehensive series of novel, unsymmetrical Malachite Green dyes containing different amino substituents has been prepared and the electronic absorption spectra have been determined. In general, the structurally unsymmetrical dyes display electronic symmetry. Hypsochromic shifts and reduced intensity of the λmax(x) absorption bands were generally observed for the dyes containing the N-methylpiperazino group, consistent with the reduced ability of the heterocyclic moiety to stabilise the cationic system by conjugation. In solvents of increasing acidity, the dyes exhibit variable spectral responses because of the differing basicities of the terminal amino groups.
Studies of Tetriary Amine Oxides. 9. Thermal Rearrangement of 1-(4-Substituted-phenyl)piperidine N-Oxides to the Corresponding N-Hydroxylamines
Khuthier, Abdul-Hussain,Al-Mallah, Khawla Y.,Hanna, Salim Y.,Abdulla, Noor-Aldeen I.
, p. 1710 - 1713 (2007/10/02)
(4-Substituted - phenyl)piperidine N-oxides undergo a thermal rearrangement to O-arylhydroxylamines.Electron withdrawing substituents are essential for the rearrangement and must be ortho or para relative to the N-O function.The reaction has been found to be first order in substrate when rates were measured in dioxane, and the activation parameters were calculated.The order of reactivity in this rearrangement is NO2 >> CN > COPh > COMe > COOEt > CONH2.The rates correlate very well with ?- constants and the ρ value was positive and large (+3.6) pointing to a highly po lar activated complex with an electron-rich reaction center.All results strongly support an intramolecular cyclic mechanism.
