321679-59-8Relevant academic research and scientific papers
Nickel-Catalyzed Intramolecular Desulfitative C - N Coupling: A Synthesis of Aromatic Amines
Chen, Xuemeng,Jia, Xiuwen,Kramer, S?ren,Li, Yue,Lian, Zhong,Liu, Jiangjun,Sun, Haotian
, p. 5702 - 5711 (2020/05/19)
A nickel-catalyzed intramolecular C - N coupling reaction via SO2 extrusion is presented. The use of a catalytic amount of BPh3 allows the transformation to take place under much milder conditions (60 °C) than previously reported C - N coupling reactions by CO or CO2 extrusion (160-180 °C). In addition, this method displays good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines, and triaryl amines. The robustness of the desulfitative C - N coupling is demonstrated by three high-yielding gram-scale reactions.
Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides
Johansen, Martin B.,Lindhardt, Anders T.
, p. 1417 - 1425 (2020/03/03)
A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.
Carbene adduct of cyclopalladated ferrocenylimine-assisted synthesis of aminopyridine derivatives by the amination of chloropyridines with primary and secondary amines
Mu, Bing,Li, Jingya,Wu, Yangjie
, p. 537 - 541 (2013/09/23)
An efficient, simple way to synthesize aminopyridine derivatives is presented, based on Buchwald-Hartwig aminations. Using 1 mol% N-heterocyclic carbene adduct of cyclopalladated ferrocenylimine in the presence of 1.5 equiv. tBuOK as base in dioxane at 110°C offered moderate to excellent yields in the reaction of chloropyridines with primary and secondary amines, including sterically hindered amines and alkyl amines. Copyright
Amination of heteroaryl chlorides: Palladium catalysis or SNAr in green solvents?
Walsh, Katie,Sneddon, Helen F.,Moody, Christopher J.
, p. 1455 - 1460 (2013/09/12)
The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SNAr reaction and N-arylation. The reaction is less satisfactory with pyridines unless an add
Cobalt-catalyzed C-N bond-forming reaction between N-aromatic 2-chlorides and secondary amines
Toma, Gabriel,Fujita, Ken-Ichi,Yamaguchi, Ryohei
scheme or table, p. 4586 - 4588 (2009/12/05)
Secondary amines react with N-aromatic 2-chlorides in the presence of a catalytic amount of cobalt chloride. When DPPP was added as ligand, the yield was further improved, The N-aromatic-containing tertiary amines formed are interesting due to their poten
