79128-83-9Relevant articles and documents
Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Li, Huaifeng,Lupp, Daniel,Das, Pradip K.,Yang, Li,Gon?alves, Théo P.,Huang, Mei-Hui,El Hajoui, Marwa,Liang, Lan-Chang,Huang, Kuo-Wei
, p. 4071 - 4076 (2021/04/12)
The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.
Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
Paudel, Keshav,Xu, Shi,Hietsoi, Oleksandr,Pandey, Bedraj,Onuh, Chuka,Ding, Keying
supporting information, p. 418 - 426 (2021/02/01)
Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.
Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles
Li, Bo,Wang, Yanxin,Chi, Quan,Yuan, Ziliang,Liu, Bing,Zhang, Zehui
, p. 4464 - 4471 (2021/03/15)
The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.
