1412903-19-5Relevant academic research and scientific papers
Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
Guan, Changwei,Feng, Yuanyuan,Zou, Gang,Tang, Jie
, p. 6906 - 6913 (2017)
N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.
O-iodoxybenzoic acid mediated N-arylation of aromatic amines by using arylhydrazines as the arylating counterpart
Jadhav, Ravindra R.,Huddar, Sameerana N.,Akamanchi, Krishnacharya G.
supporting information, p. 6779 - 6783 (2013/11/06)
Through free-radical trapping experiments we have established, for the first time, the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation of aryl free radicals. On the basis of this finding, a method was developed for the N-arylation of aromatic amines under mild conditions (base-free, -5 °C) by using arylhydrazines as the arylating counterpart and arylamines. The scope of this method was demonstrated by using a number of arylhydrazines and arylamines, which gave the N-arylated amines in good yields. Through free-radical trapping experiments, the present work describes the combination of arylhydrazines with o-iodoxybenzoic acid (IBX) for the generation aryl free radicals. This finding is exploited in the development of a mild method for the N-arylation of arylamines by using arylhydrazines as the arylating agents. The scope of this method is demonstrated through a number of examples. Copyright
Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
Samblanet, Danielle C.,Schmidt, Joseph A. R.
, p. 7 - 18,12 (2012/12/12)
While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.
