JOURNAL OF ORGANIC CHEMISTRY
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2021
·
IF 4.354
Hao Song,Yao Xiao,Zhuohua Zhang,Wanjin Xiong,Ren Wang,Liangcheng Guo,Taigang Zhou
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.
研究领域:
有机化学
·
催化化学
✓ 已验证
DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2019
·
IF 8.355
Gang Wang,Zengxi Li,Liu Fan,Chunshan Li,Suojiang Zhang
S ec -amines catalyzed two-step Mannich reaction for preparation of methacrolein from propionaldehyde and formaldehyde was more attractive than the C 4 selective oxidation route. Herein, a novel continuous fixed-bed process was developed for direct preparation of methacrolein from above stocks with catalysis of sec -amine grafted D301 resin. The effect of resin, sec -amine structure and grafting percentage on catalytic performance of the modified resin were detailed investigated and demonstrated by using FT-IR, TG-DTA, titration and solid-state NMR characterization methods before the optimal conditions were obtained. The grafting percentage of amine with abundant sec -amino groups onto D301 resin could reach 93.7% at optimal condition. With this new strategy, the yield and selectivity of methacrolein could attain 40.2% and 99.3%. In addition, the Mannich reaction step with activation energy of 66.3 kJ/mol was determined as the rate-controlling step through mechanism-based kinetic calculation.
研究领域:
有机化学
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催化化学
✓ 已验证
DOI
高影响因子
ChemPlusChem
·
2020
·Vol. 85
·期 8
·1783-1788
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IF 2.753
Rongxiu Guo,GuangQi He,Lei Liu,Yongjian Ai,Ze-nan Hu,Xinyue Zhang,Haimeng Tian,Hong-bin Sun,Dun Niu,Qionglin Liang
Graphical Four in one : A quaternary-component catalyst containing platinum, copper, and iron, which are supported on Fe 3 O 4 nanospheres can be used in the selective synthesis of symmetrical secondary amines by transfer hydrogenation of nitriles with excellent conversion and selectivity. A variety of nitriles were tested for the synthesis of symmetrical secondary amines, and no hydrogenolysis byproducts were detected. Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt−CuFe/Fe 3 O 4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h −1 . A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.
研究领域:
催化化学
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绿色化学
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材料科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2024
·
IF 13.3
Xiuqin Ci,Dong Zhai,Rui Tu,Xiaoju Li,Shuchao Jiang,Xinbo Wang,Weiqiao Deng,Guoqing Ren
CO 2 hydrogenation into formic acid is of great significance to mitigate CO 2 emission. However, conventional routes typically require the addition of unrecyclable bases to shift the reaction equilibrium by the formation of formate, which leads to complex subsequent separation and difficulty in continuous production of pure formic acid solution. Here we report a secondary amine-modified PdMn nanocatalyst for the continuous production of pure formic acid solution in fixed-bed reactors via CO 2 hydrogenation. By optimizing fine structure of PdMn nano-alloy, the optimal TOF of up to 26.5 h −1 is obtained under mild reaction conditions (25 ℃, 3.0 MPa). This is one of the highest levels reported for a heterogeneous catalyst without alkali additives under similar conditions. The characterization shows that the two-component alloying effect of PdMn and the synergistic effect between PdMn NPs and secondary amine group (NH) are the key to obtaining superior reactivity. These findings in this work may pave an avenue for conversion of CO 2 in a more environmentally friendly way.
研究领域:
化学工程
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环境科学
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催化材料
✓ 已验证
产品关联
DOI
高影响因子
Catalysts
·
2021
·Vol. 11
·期 2
·287
·
IF 4.146
Jianguo Liu,Mingyue Zhang,Longlong Ma
Dibenzylamine motifs are an important class of crucial organic compounds and are widely used in fine chemical and pharmaceutical industries. The development of the efficient, economical, and environmentally friendly synthesis of amines using transition metal-based heterogeneous catalysts remains both desirable and challenging. Herein, we prepared the covalent organic framework (COF)-supported heterogeneous reduced COF-supported Pd-based catalyst and used it for the one-pot reductive amination of aldehydes. There are both Pd metallic state and oxidated Pdσ+in the catalysts. Furthermore, in the presence of the reduced COF-supported Pd-based catalyst, many aromatic, aliphatic, and heterocyclic aldehydes with various functional groups substituted were converted to their corresponding amines products in good to excellent selectivity (up to 91%) under mild reaction conditions (70 °C, 2 h, NH3, 20 bar H2). This work expands the covalent organic frameworks for the material family and its support catalyst, opening up new catalytic applications in the economical, practical, and effective synthesis of secondary amines.Keywords:COF;reduced COF-supported Pd-based catalyst;reductive amination;secondary amines
研究领域:
催化
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有机化学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
APPLIED CATALYSIS A-GENERAL
·
2022
·
IF 5.723
Yushan Yang,Shaoyu Yuan,Heli Pan,Zixuan Li,Zejiang Li,Sufang Sun,Yongjun Gao
A novel explosion-assistant strategy was developed to fabricate graphene oxide supported nickel and palladium three-component catalyst Pd/Ni/NiO/GO for hydrogenation of nitriles to secondary amines. The explosion during the synthesis of catalyst was essential to the well-dispersion of palladium and the decomposition of metal salt precursors. Palladium component was well anchored on nickel oxide and graphene oxide sheets, which regulated the catalytic performance of palladium. This special structure facilitated the spillover of active hydrogen species generated on palladium component to nickel (oxide) and graphene oxide sheets, enhancing the catalytic activity of the bimetallic catalyst. This work developed an effective strategy to fabricate multi-component metal catalyst with low-cost transition metal as main composition for selective hydrogenation of nitriles to secondary amines.
研究领域:
催化
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化学工程
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材料科学
✓ 已验证
产品关联
DOI
高影响因子
LETTERS IN ORGANIC CHEMISTRY
·
2025
·Vol. 22
·期 8
·633-641
·
IF 1
Hongyin Wang,Yu Liang,Yida Yu,Yihao Wang,Ni An,Dong Cai
The ureido moiety stands as one of the most regarded scaffolds in medicinal and organic synthesis. In this study, we endeavored to synthesize a product containing tertiary amine moieties through the nucleophilic substitution reaction of the 2-chloroethyl urea derivative with a secondary amine, utilizing either inorganic bases, such as K2CO3 or organic bases like triethylamine as acid-binding agents in diverse reaction media. Unfortunately, the reaction failed to yield the desired nucleophilic substitution product in high yield, attributed to the reactivity of the 2-chloroethyl urea derivative. The structures of potential impurities were elucidated based on comprehensive spectroscopic data, including 1H NMR, 13C NMR, HRMS, HMBC, and HSQC.
研究领域:
药物化学
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有机合成
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亲核取代反应
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化学反应优化
✓ 已验证
产品关联
DOI
高影响因子
Journal of CO2 Utilization
·
2018
·
IF 5.503
Dandan Song,Di Li,Xuan Xiao,Chen Cheng,Somboon Chaemchuen,Ye Yuan,Francis Verpoort
A green and recyclable catalytic system based on AgBr and an ionic liquid (IL) was developed for the three-component coupling reaction of propargylic alcohols, secondary amines and carbon dioxide (CO 2 ). A series of target carbamates, especially those generated from challenging substrates, could be obtained smoothly at atmospheric CO 2 pressure in a straightforward one-pot process. Moreover, the catalyst loading reached the lowermost level ever reported. Particularly, this catalytic system exhibited robust constancy and could be reused at least 5 times with retention of high catalytic activity. It is worth noting that this is the first catalytic system which could be recycled successfully for this reaction.
研究领域:
化学
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催化
·
绿色化学
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有机合成
✓ 已验证
产品关联
DOI
高影响因子
CRYSTENGCOMM
·
2020
·Vol. 22
·期 15
·2642-2648
·
IF 3.117
Ming-Yu Dou,Xian-Qiang Huang,Guo-Yu Yang
By the combination of Ag-complexes and Keggin POMs, two novel inorganic–organic silver–polyoxometalates hybrids, [Ag3L2(DMSO)2][PW12O40]·4DMSO (1) and [(Ag2L2)2][SiW12O40]·10DMSO·2H2O (2) (L = 4-(2-pyridyl)-6-(4-pyridyl)-2-aminopyrimidine), were synthesized and characterized. Interestingly, the silver atoms in compound 1 are three-coordinated with the AgNO model; however, the Ag atoms of compound 2 were surrounded by four N atoms of the organic ligands and displayed a distorted tetrahedral configuration. Importantly, compound 1 showed high catalytic activities for the three-component coupling reaction of alkynes and secondary amines along with formaldehyde, which resulted in a series of propargylamine derivatives in higher yields (up to 99%). Furthermore, the Ag–POM catalyst was easily recovered by filtration and reused for three cycles without a significant loss in catalytic activity. A tentative mechanism is also proposed for this transformation.
研究领域:
无机化学
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有机化学
·
催化
✓ 已验证
产品关联
DOI
高影响因子
GREEN CHEMISTRY
·
2022
·Vol. 24
·期 18
·6945-6954
·
IF 11.034
Songtao Huang,Zijiang Zhao,Zhongzhe Wei,Mingxuan Wang,Yi Chen,Xiaosa Wang,Fangjun Shao,Xing Zhong,Xiaonian Li,Jianguo Wang
Imines and secondary amines have attracted widespread attention in the fields of medicine owing to their unique unit structures and biological activities. However, the design of catalysts for the targeted syntheses of imines and secondary amines presents challenges due to the uncontrollable cascade reaction of nitrobenzene (NB) and benzaldehyde (BA). Herein, we report that carbon-coated Co and PtCo catalysts (Co/SiO2@CN and PtCo/SiO2@CN) realize the directional synthesis of imines and secondary amines under the same conditions, respectively, through the synergistic action of the active components. The superior catalytic performance benefited from the integrated geometric and electronic effects. Specifically, the uniformly coated nitrogen-doped carbon drives the adsorption ability of NB more strongly than BA and inhibits the formation of benzyl alcohol. For Co/SiO2@CN, Co–Nx and metallic Co synergistically promote the highly selective synthesis of imines with much higher conversion (97%) and selectivity (98%) than most Co-based catalysts at 60 °C. For PtCo/SiO2@CN, the electron transfer between Pt and Co promotes the hydrogen spillover ability and enables it to afford 100% BA conversion and 100% secondary amine selectivity, reaching the TOF value of 296 h−1. This synthesis strategy provides an advanced concept for designing chemoselective catalysts, which has important implications for both scientific research and industrial applications.
研究领域:
催化
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有机化学
·
材料科学
·
药物化学
✓ 已验证
产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2017
·
IF 3.671
Wei Wang,Qian Bai,Tao Liang,Huiyu Bai,Xiaoya Liu
The modification of regenerated cellulose (RC) membranes was carried out by using silane coupling agents presenting primary and secondary amino-groups. The grafting of the amino groups onto the modified cellulose molecule was confirmed by X-ray photoelectron spectroscopies and 13 C nuclear magnetic resonance spectroscopic analyses. The crystallinity of the cellulose membranes (CM) decreased after chemical modification as indicated by the X-ray diffraction results. Moreover, a denser structure was observed at the surface and cross section of the modified membranes by SEM images. The contact angle measurements showed that the silane coupling treatment enhanced the hydrophobicity of the obtained materials. Then the catalytic properties of two types of modified membranes were studied in a batch process by evaluating their catalytic performance in a Knoevenagel condensation . The results indicated that the cellulose membrane grafted with many secondary amines exhibited a better catalytic activity compared to the one grafted only by primary amines. In addition, the compact structure of the modified membranes permitted their application in a pervaporation catalytic membrane reactor. Therefore, functional CM that prepared in this paper represented a promising material in the field of industrial catalysis.
研究领域:
材料科学
·
化学工程
·
催化
·
膜技术
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）