55096-86-1Relevant articles and documents
Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
Song, Hao,Xiao, Yao,Zhang, Zhuohua,Xiong, Wanjin,Wang, Ren,Guo, Liangcheng,Zhou, Taigang
, p. 790 - 800 (2022/01/11)
A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.
Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines
Han, Zhangang,Hao, Zhiqiang,Lin, Jin,Lu, Guo-Liang,Zhang, Junhua,Zhang, Xiaoying
, p. 3843 - 3853 (2021/11/18)
Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.
One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt-Fe3O4nanoparticle catalyst
Byun, Sangmoon,Cho, Ahra,Cho, Jin Hee,Kim, B. Moon
, p. 4201 - 4209 (2020/09/23)
We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt-Fe3O4 nanoparticle (NP) catalyst. The use of a bimetallic catalyst resulted in enhanced reactivity and selectivity compared to that of either monometallic Pd-Fe3O4 or the Pt-Fe3O4 NP catalyst. Using this bimetallic catalytic system, we were successful in the synthesis of various unsymmetrical secondary amines under mild conditions. However, aryl nitriles containing an electron-donating substituent were rather resistant to the reductive amination, and when hexafluoroisopropanol (HFIP) was used as a co-solvent, the reaction selectivity and yield for unsymmetrical secondary amines increased dramatically. Using the catalyst system, one-pot, gram-scale synthesis of indole was possible from 2-nitrophenylacetonitrile. Due to the magnetic property of the Fe3O4 support, the bimetallic catalyst could easily be recycled using an external magnet at least four times.
