103796-64-1Relevant articles and documents
AROMATIC NUCLEOPHILIC SUBSTITUTIONS WITH o- AND p-FLUORONITROBENZENES IN APROTIC SOLVENTS. STERIC EFFECTS ON THE BASE-CATALYSED STEP
Nudelman, Norma S.,Cerdeira, Silvia
, p. 695 - 698 (1986)
The kinetics of the reaction between o- and p-fluoronitrobenzene with n- and iso-propylamine were studied in toluene and DMSO at several amine concentrations and temperatures in the range 30-100 deg C.The results show that, contrary to the previous assumption, primary steric effects due to branching in the amine do not produce a large decrease in the reaction rate when the first step is rate determining.However, reactions with bulky amines can be extremely slow because of the reduced power of the amine as a hydrogen-bond acceptor catalyst, when the second step is rate determining.The reaction rate may be increased by the addition of a non-nucleophilic base or another hydrogen-bond acceptor catalyst such as dimethyl sulphoxide.
A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
supporting information, p. 5222 - 5229 (2021/07/29)
Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
Para-Nitroaniline-functionalized chromophoric organic-inorganic hybrid materials
Ladewig, Katharina,Seifert, Andreas,Hahn, Harald,Hietschold, Michael,Moszner, Norbert,Burtscher, Peter,Spange, Stefan
experimental part, p. 3839 - 3852 (2012/05/31)
An advanced procedure for the one-pot synthesis of organic-inorganic hybrid materials via combination of sol-gel process and nucleophilic aromatic substitution reaction (SNAr) of 4-fluoronitrobenzene and 3-aminopropyltrimethoxysilane is described. With this advanced procedure both SNAr-reaction and sol-gel process can be accomplished in the same reaction vessel due to the sol-gel precursor tetraethoxysilane (TEOS) acting as solvent during the first reaction step. Via extensive NMR spectroscopic studies it is proven for the first time that - contrary to common belief - hydrogen fluoride (HF), which is formed as a by-product in the SNAr-reaction, is not trapped by any bases present but is rather trapped by both of the silane species and serves as a catalyst during the subsequent sol-gel process. The chromophoric system of the resulting xerogels is well protected against aggressive chemicals, i.e. strong acids, by the silica matrix, which predestines these materials for pigment applications. Given that a high chromophore content is highly desirable in these applications, we show that the chromophore content of the final xerogel can be varied by modification of the organosilicon precursor:TEOS ratio or by using trialkoxy-silanes bearing two or three amino functions, whereby the latter option is more favourable. Monodisperse core-shell particles with identical chromophore content but consisting of a pure silica-core and a p-nitroaniline functionalized shell with a diameter of about 200 nm can also be prepared using this advanced procedure.
A reductive amination of carbonyls with amines using decaborane in methanol
Bae, Jong Woo,Lee, Seung Hwan,Cho, Young Jin,Yoon, Cheol Min
, p. 145 - 146 (2007/10/03)
Aldehydes and ketones were easily converted to the corresponding amines by the reaction of amines in methanol using decaborane (B10H14) at room temperature under nitrogen. The reaction is simple and efficient. The Royal Society of Chemistry 2000.
