34143-87-8Relevant academic research and scientific papers
Rational Design of Cobalt-Platinum Alloy Decorated Cobalt Nanoparticles for One-Pot Synthesis of Imines from Nitroarenes and Aldehydes
Gong, Wanbing,Han, Miaomiao,Chen, Chun,Lin, Yue,Wang, Guozhong,Zhang, Haimin,Zhao, Huijun
, p. 5948 - 5958 (2020)
Developing high-performance heterogeneous catalysts for one-pot reductive amination reactions is critically important for pharmaceutical and agrochemical synthetic industries. In this work, N-doped carbon nanotubes supported CoPt alloy decorated Co nanoparticles (NPs) are successfully fabricated. As a consequence, the resultant catalyst exhibits desirable activity, selectivity and stability toward the one-pot synthesis of imines. More importantly, the extensive experimental studies and density function theory (DFT) calculations results reveal that the high catalytic activity of the catalyst is mainly due to the co-existence of CoPt alloy NPs and Co NPs with Co?Nx active sites. The high selectivity of imines could be ascribed to the following aspects: (1) competitively preferred adsorption of nitroarenes to avoid side-hydrogenation of aldehydes; (2) weakened adsorption of imines to minimize its over-hydrogenation. This work may provide a promising direction and strategy to design high-performance reductive amination catalysts for industrial applications.
Selective Encapsulation and Unusual Stabilization of cis-Isomers by a Spherical Polyaromatic Cavity
Yuasa, Mana,Sumida, Ryuki,Tanaka, Yuya,Yoshizawa, Michito
, (2022/02/02)
To explore new cavity functions, we herein employed cis-trans stereoisomers with a N=N, C=C, or C=N unit as guest indicators for a polyaromatic capsule. Thanks to the rigid, spherical cavity with a diameter of ～1 nm, azobenzene and stilbene derivatives ar
Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles
Jin, Ruo-Xing,Dai, Jing-Cheng,Li, Yan,Wang, Xi-Sheng
supporting information, p. 421 - 426 (2021/01/26)
The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.
Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles
Wang, Kai,Wei, Tingting,Zhang, Yujia,Hou, Jiahao,Bai, Renren,Xie, Yuanyuan
, p. 1787 - 1794 (2021/03/14)
A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.
Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives
Cheng, Biao,Lyu, Hairong,Quan, Yangjian,Xie, Zuowei
supporting information, p. 7930 - 7933 (2021/08/17)
A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.
Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines
Wu, Di,Bu, Qingqing,Guo, Cheng,Dai, Bin,Liu, Ning
, (2021/02/02)
Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.
Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission
Jiang, Heyan,Sheng, Meilin,Li, Yue,Kong, Shuzhen,Bian, Fengxia
, (2021/05/17)
Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/
One-Pot Synthesis of Schiff Bases by Defect-Induced TiO2- x-Catalyzed Tandem Transformation from Alcohols and Nitro Compounds
Chen, Liyong,Fang, Qiang,Shen, Xiaoshuang,Tong, Jing,Wang, Jinfeng,Wang, Yao,Zhang, Hui
supporting information, p. 10715 - 10721 (2021/07/26)
Schiff bases that are generally formed from condensation reactions of aldehydes (or ketones) and amino groups could also be produced by a photodriven one-pot tandem reaction between alcohols and nitro compounds, in our case. Herein, TiO2-x porous cages derived from NH2-MIL-125 by a self-sacrificing template route are used to study the organic transformation and exhibit 100% conversion efficiency of nitrobenzene and 100% selectivity for Schiff bases in the system of benzyl alcohol (5 mL) and nitrobenzene (41 μL) upon light irradiation, but hydrogen by dehydrogenation of benzyl alcohol cannot be detected. Successful occurrence of the organic transformation is mainly attributed to Ti(III)-oxygen vacancy associates. Surface oxygen vacancy-related Ti(III) sites are responsible for binding with nitro groups, and low-coordinated Ti5c sites selectively adsorb hydroxyl groups of benzyl alcohol. The Ti(III) and oxygen vacancy associates capture photogenerated electrons for achievement of multielectron reduction of nitrobenzene and the subsequent Schiff base condensation reaction with the as-formed benzaldehyde.
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.
Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles
Wu, Jiajun,Darcel, Christophe
, p. 1023 - 1036 (2021/01/09)
A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.
