5338-39-6Relevant academic research and scientific papers
N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)
Wei, Dongyue,Yang, Peng,Yu, Chuanman,Zhao, Fengkai,Wang, Yilei,Peng, Zhihua
supporting information, p. 2254 - 2263 (2021/02/26)
A manganese-catalyzed N-alkylation reaction of amines with alcohols via hydrogen autotransfer strategy has been demonstrated. The developed practical catalytic system including an inexpensive, nontoxic, commercially available MnCl2 or MnBr(CO)5 as the metal salt and triphenylphosphine as a ligand provides access to diverse aromatic, heteroaromatic, and aliphatic secondary amines in moderate-to-high yields. In addition, this operationally simple protocol is scalable to the gram level and suitable for synthesizing heterocycles such as indole and resveratrol-derived amines known to be active for Alzheimer's disease.
Iridium(III)- benzoxazolyl and benzothiazolyl phosphine ligands catalyzed versatile alkylation reactions with alcohols and the synthesis of quinolines and indole
Huang, Shuang,Wu, Si-Peng,Zhou, Quan,Cui, He-Zhen,Hong, Xi,Lin, Yue-Jian,Hou, Xiu-Feng
, p. 14 - 23 (2018/05/22)
A series of benzoxazolyl and benzothiazolyl phosphine ligands 4a-4g were synthesized and characterized, which prepared from commercially available 2-aminophenol/2-aminobenzenethiol and 2-bromobenzaldehyde via cyclization and phosphination. The representative ligands 4c and 4e were determined by single-crystal X-ray diffraction. The corresponding iridium complexes could be generated in situ when [Cp*IrCl2]2 (Cp* = pentamethylcyclopentadienyl) encountered ligands. The molecular structures of complexes 5c and 5e were crystallographically characterized. The dihedral angles of N (1)-C (1)-C (8)-C (9) showed an increasing twist compared with the corresponding ligand. The iridium (III) catalysts were screened, [Cp*IrCl2]2/4a proved to be the optimal catalyst, which exhibited efficient catalytic activity toward versatile alkylations including ketones, secondary alcohols and amines with primary alcohols. Additionally, the synthesis of quinolines from ketones with 2-aminobenzyl alcohol by intermolecular cyclization and indole from 2-(2-aminophenyl)ethanol by intramolecular cyclization were achieved under the optimized conditions.
Pd/C as an Efficient and Reusable Catalyst for the Selective N-Alkylation of Amines with Alcohols
Liu, Xiang,Hermange, Philippe,Ruiz, Jaime,Astruc, Didier
, p. 1043 - 1045 (2016/04/05)
An efficient Pd/C-catalyzed synthesis of secondary amines involving C-N bond formation was achieved from amines and alcohols with H2O as the only byproduct. This common, green, commercial, and cheap catalyst was recycled five times in this sustainable, simple, and economic procedure.
Synthesis of benzidine derivatives via FeCl3·6H 2O-promoted oxidative coupling of anilines
Ling, Xuege,Xiong, Yan,Huang, Ruofeng,Zhang, Xiaohui,Zhang, Shuting,Chen, Changguo
, p. 5218 - 5226 (2013/07/25)
Under open-flask conditions in the presence of commercially available FeCl3·6H2O, N,N-disubstituted anilines can be converted into diversely functionalized benzidines with yields of up to 99%. Oxidative coupling was extended to N-monosubstituted anilines, and the method was applied to the efficient preparation of 6,6′-biquinoline. Mechanistic investigations have also been performed to explain the observed reactivities.
