588-47-6Relevant articles and documents
Cobalt encapsulated in N?doped graphene sheet for one-pot reductive amination to synthesize secondary amines
Liu, Lin,Li, Wenxiu,Qi, Ran,Zhu, Qingqing,Li, Jing,Fang, Yuzhen,Kong, Xiangjin
, (2021/03/14)
To develop an efficient base-metal reductive amination catalyst for synthesis of secondary amines is still a major challenge. In this study, an efficient N-doped graphene sheet-coated cobalt catalyst (Co@CN-800) was developed through a simple pyrolysis process, which could gave 99.5 % yield of N-benzylaniline by one-pot reductive amination of nitrobenzene with benzaldehyde during at least 5 cycles. Catalyst characterization and control experiments confirmed that the robust catalytic performance of the catalyst is probably due to the synergy effect of in situ generated Co-Nx encapsulated in N?doped graphene layer and appropriate meso-pore structure. Additionally, The substrate adaptability of the catalyst was proved since a variety of corresponding secondary amines were smoothly obtained under relatively mild conditions, which makes the secondary amine synthesis strategy based on Co@CN-800 shows excellent application prospect.
Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols
Huang, Ming,Li, Yinwu,Lan, Xiao-Bing,Liu, Jiahao,Zhao, Cunyuan,Liu, Yan,Ke, Zhuofeng
supporting information, p. 3451 - 3461 (2021/05/03)
Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.
Direct N-Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition-Metal-Free Catalysis
Lu, Chunlei,Qiu, Zetian,Xuan, Maojie,Huang, Yan,Lou, Yongjia,Zhu, Yiling,Shen, Hao,Lin, Bo-Lin
supporting information, p. 4151 - 4158 (2020/08/21)
A scalable protocol of direct N-mono/di-alkyl/fluoroalkylation of primary/secondary amines has been constructed with various carboxylic acids as coupling agents under the catalysis of a simple air-tolerant inorganic salt, K3PO4. Advantageous features include 100 examples, 10 drugs and drug-like amines, fluorinated complex tertiary amines, gram-scale synthesis and isotope-labelling amine, thus demonstrating the potential applicability in industry of this methodology. The involvement of relatively less reactive silicon-hydride compared with the traditional reactive metal-hydride or boron-hydride species required to reduce the amide intermediates presumably contributes to the remarkable functional group compatibility. (Figure presented.).
