107455-62-9Relevant articles and documents
Unexpected multicomponent reaction of 2/4-methoxyarylaldehydes with arylhydroxylamines and maleic anhydride: a novel synthesis of unsymmetrical diarylamines
Sridharan,Karthikeyan,Muthusubramanian
, p. 4221 - 4223 (2006)
Unsymmetrical diarylamines have been synthesized by a novel, unexpected multicomponent reaction between methoxyarylaldehydes, N-arylhydroxylamine and maleic anhydride. A possible mechanism for the formation of the product is proposed. The reaction was also carried out under microwave irradiation.
A highly active palladium catalyst system for the arylation of anilines
Sadighi, Joseph P.,Harris, Michele C.,Buchwald, Stephen L.
, p. 5327 - 5330 (1998)
The chelating ligand bis[2-(diphenylphosphino)phenyl] ether (DPEphos), in combination with palladium acetate, forms a highly active catalyst system for the coupling of anilines with aryl bromides. The bisphosphine is easily prepared in large quantity and
The First Rapid Palladium-Catalyzed Aminations of (Azahetero)aryl Chlorides under Temperature-Controlled Microwave Heating
Maes, Bert U. W.,Loones, Kristof T. J.,Lemière, Guy L. F.,Dommisse, Roger A.
, p. 1822 - 1825 (2003)
Fast palladium-catalyzed animations of activated and unactivated azaheteroaryl chlorides as well as unactivated aryl chlorides have been achieved using temperature-controlled microwave heating. Good yields (75-91%) were obtained in a reaction time of only 10 minutes.
Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles
Zhang, Maoyuan,Xu, Zengbing,Shi, Dabin
, (2020/12/25)
A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated, giving the desired coupling products in good to excellent yields (62–94%). The method is practical and offers an alternative to the corresponding copper-catalyzed Chan-Evans-Lam process for the construction of C–N bonds.
Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines
Chen, Kai,Chen, Wanzhi,Chen, Wei,Liu, Miaochang,Wu, Huayue
, p. 8110 - 8115 (2019/08/26)
The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.
Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
, p. 4891 - 4900 (2018/11/21)
A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
