79128-83-9Relevant academic research and scientific papers
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.
Structures and catalytic oxidative coupling reaction of four Co-MOFs modified with R-isophthalic acid (R=H, OH and COOH) and trigonal ligands
Bao, Yu-Mei,Deng, Wei,Liu, Qing,Liu, Zhen-Jiang,Xing, Yuan-Yuan,Zhang, Jian-Yong,Zhang, Lin-Yan,Zhang, Na
, p. 7590 - 7601 (2021/11/17)
In this paper, we present fourCo-MOFsusing R-substituted isophthalic acid (R-H2BDC, R = H, OH and COOH) along with trigonaln-TBT (n= 3 or 4) as organic ligands. TheseCo-MOFsare formulated as {[Co(1,3-BDC)(4-TBT)2/3]·(H2O)(DMF)1.5}n(Co-MOF-1), {[Co(HO-BDC)(4-TBT)]·(EtOH)2(DMF)2}n(Co-MOF-2), {[Co(HO-BDC)(4-TBT)2/3]·(H2O)3(MeOH)3(DMA)}n(Co-MOF-3) and{[Co3(BTC)2(3-TBT)2(H2O)2]·(H2O)2(EtOH)5(DMA)1.5}n(Co-MOF-4), where H2BDC = isophthalic acid, OH-H2BDC = 5-hydroxyisophthalic acid and H3BTC = 1,3,5-tricarboxybenzene, 4-TBT = 1,3,5- tris(4-pyridyl)benzene and 3-TBT = 1,3,5-tris(3-pyridyl)benzene.Co-MOF-1,2and3are constructed from the dimeric Co2(COO)2unit and exhibit 3D frameworks. InCo-MOF-4, the dimeric Co2(COO)2unit and single nuclear CoIIcenter are connected by BTC3?and 3-TBT ligands into a 3D network. The catalytic experiments revealed that fourCo-MOFscan catalyze the oxidative coupling reaction of benzyl alcohols and aniline to imines with good to excellent conversions under solvent-free conditions and an air atmosphere.Co-MOF-4exhibited the best catalytic performance and the catalyst could be reused for at least five cycles without losing its structural integrity and catalytic activity.
Integrated Flow Synthesis of α-Amino Acids byIn SituGeneration of Aldimines and Subsequent Electrochemical Carboxylation
Naito, Yuki,Nakamura, Yuto,Shida, Naoki,Senboku, Hisanori,Tanaka, Kenta,Atobe, Mahito
, p. 15953 - 15960 (2021/07/20)
The synthesis of α-amino acids was carried out in a continuous flow system. In this system, aldimines were efficiently generatedin situvia the dehydration-condensation of aldehydes with anilines in a desiccant bed column filled with 4 ? molecular sieves d
Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams
Ye, Jian-Heng,Bellotti, Peter,Paulisch, Tiffany O.,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 13671 - 13676 (2021/05/11)
We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.
Aza-peterson olefinations: Rapid synthesis of (E)-alkenes
Britten, Thomas K.,Basson, Ashley J.,Roberts, Dean D.,McLaughlin, Mark G.
, p. 3535 - 3544 (2021/06/03)
An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.
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.
Fe2Mn(μ3-O)(COO)6 Cluster Based Stable MOF for Oxidative Coupling of Amines via Heterometallic Synergy
Wang, Ying-Xia,Wang, Hui-Min,Meng, Pan,Song, Dong-Xia,Qi, Zhikai,Zhang, Xian-Ming
, p. 2983 - 2989 (2021/08/30)
The direct catalytic oxidative coupling of amines is one of the attracting methods for the synthesis of a variety of pharmaceutical or industrial needed imines. Numerous earth-abundant manganese based salts, oxides, and complexes have been applied in this reaction. However, these compounds suffered from difficult separation, large catalyst loading, complicated reactivation or indeterminate activity. Considering the facts that metal-organic frameworks (MOFs) with crystalline structure, precise composition, and enormous surface area have superior performance in heterogeneous catalytic reactions, herein, we introduced Mn into [Fe3(μ3-O)(CH3COO)6], one of the precursors for the preparation of stable MOFs, and got [Fe2Mn(μ3-O)(CH3COO)6] cluster. After ligand replacement with biphenyl-3,4’,5-tricarboxylic acid (BPTC), heterometallic cluster-based [Fe2Mn(μ3-O)(BPTC)2(DMF)2(H2O)] (1) was obtained. As expected, 1 is stable and able to catalyze the homo- or cross-coupling of amines effectively and selectively with 0.9 mol% catalyst loading at room temperature. Control experiments indicated that the catalytic activity of 1 mainly stems from Mn sites and that Fe synergistically contributes to the stability. Additionally, 1 is recyclable and can be reused easily for at least 8 runs without obvious decrease in catalytic ability. To our knowledge, 1 should be the first heterometallic cluster-based MOF with defined structure suitable for the synthesis of diverse imines from oxidative coupling of amines under mild conditions, which may shed light on the easy preparation of effective heterogeneous catalysts for organic synthesis.
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.
Method for synthesizing aluminum phosphate molecular sieve catalytic imine
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Paragraph 0032-0034, (2020/06/02)
The invention discloses a method for catalyzing synthesis of an imine by using an aluminum phosphate molecular sieve, and belongs to the technical field of catalytic synthesis of imines. Under the action of an HP-MeAlPO-5 molecular sieve, air or oxygen is used as an oxidant, and an amine and an alcohol which contain different substituents are directly subjected to oxidative coupling to synthesizethe imine under mild conditions. According to the method provided by the invention, the reaction conditions of the adopted catalytic system are mild, and the TOF is high; a reaction can efficiently catalyze the synthesis of the imine at room temperature under air; and the method can adopt transition metals, which are cheap and easy to obtain, such as iron, cobalt and nickel as a molecular sieve dopant, and the availability of the molecular sieve is improved.
Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ
Xiong, Ruimei,Hussain, Muhammad Ijaz,Liu, Qing,Xia, Wen,Xiong, Yan
supporting information, (2019/12/11)
A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.
