107735-33-1Relevant academic research and scientific papers
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0047; 0053-0056; 0059, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
CuI/2-Aminopyridine 1-Oxide Catalyzed Amination of Aryl Chlorides with Aliphatic Amines
Chen, Xiahong,He, Yongqiang,Liang, Yun,Liu, Wenjie,Wang, Deping,Xia, Xiaohong,Xu, Jiamin,Xu, Zhifeng,Zhang, Fuxing,Zhang, Xin
supporting information, p. 7486 - 7490 (2020/10/12)
A class of 2-aminopyridine 1-oxides are discovered to be effective ligands for the Cu-catalyzed amination of less reactive (hetero)aryl chlorides. A wide range of functionalized (hetero)aryl chlorides reacted with various aliphatic amines to afford the desired products in good to excellent yields under the catalyst of CuI/2-aminopyridine 1-oxides. Furthermore, the catalyst system worked well for the coupling of cyclic secondary amines and N-methyl benzylamine with (hetero)aryl chlorides.
Evaluation of the Polar-Inductive and Mesomeric Effects exerted on Contiguous Functionalities by N-Oxidopyridinium Groups
Barchiesi, Emma,Bradamante, Silvia,Carfagna, Carla,Ferraccioli, Raffaella,Giorgio, A.,Pagni, Giorgio A.
, p. 1009 - 1014 (2007/10/02)
The polar-inductive and mesomeric effects (and mixtures thereof) of N-oxipyridinium-2-, -3-, and 4-yl functionalities have been evaluated in terms of the δIB, δR-, and δ-C scales previously defined.Values were generated fr
On the Structure of Carbamoylated 2-Phenylaminopyridines
Morkved, Eva H.
, p. 393 - 400 (2007/10/02)
Unambiguous preparations of 2-(N-alkoxycarbonyl-N-phenyl)aminopyridine 1-oxides are used to prove that the product from 2-phenylaminopyridine 3 and phenyl isocyanate is the expected urea 2a.Recently a 1,2-dihydropyridine derivative 1 has been claimed to be the product from 3 and phenyl isocyanate.The exocyclic nitrogen of 3 invariably reacts as the nucleophile towards electrophiles such as carbonyl chloride, esters of chloromethanoic acid and aryl isocyanates. 1H n.m.r. and 13C n.m.r. spectra support the assigned structures of the products from these reactions.
