NEW JOURNAL OF CHEMISTRY
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2022
·Vol. 46
·期 11
·5312-5320
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IF 3.925
Keping Wang,Mei Wu,Yixuan Liu,Ying Yang,Hu Li
Five-membered nitrogen heterocyclic pyrroles have extremely high physiological activity and are widely used in medicine, agriculture, materials chemistry, industry, and supramolecular chemistry. Developing a mild and eco-friendly way to synthesize functionalized pyrroles from biologically derived materials is desirable. In this study, biomass-derived 2,5-dimethylfuran can react with a series of aromatic amines to synthesize 2,5-dimethyl-N-arylpyrroles through acid-enabled ring-opening and Paal–Knorr condensation in one pot. Among the tested acid catalytic materials, a new magnetic biocarbon-based sulfonic acid solid catalyst (WK-SO3H) showed excellent catalytic performance in the synthesis of N-substituted pyrroles (up to ca. 90% yield) and was easy to separate and recover by an external magnetic field. The ring-opening of furan proved to be the rate-determining step of the above one-pot multi-step conversion process, and 2,5-hexanedione is a key intermediate for the cascade reaction, while the addition of water could significantly enhance the above-mentioned ring-opening reaction. Furthermore, multiple characterization methods (e.g., FT-IR, TGA, XRD, NH3-TPD, and XPS) confirmed that WK-SO3H has good stability in the aqueous reaction system.
研究领域:
有机化学
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生物化学
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材料科学
✓ 已验证
产品关联
DOI
高影响因子
APPLIED CATALYSIS B-ENVIRONMENTAL
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2022
·
IF 24.319
Xiang Li,Likang Zhang,Zeliang Wu,Shixia Chen,Jun Wang,Zheling Zeng,Ji-Jun Zou,Shuguang Deng,Qiang Deng
Herein, an efficient domino synthesis for N-aryl pyrroles and tetrahydropyrroles from biomass-derived furan alcohols (i.e., 5-methyl furfuryl alcohol, and 2,5-bis(hydroxymethyl)furan) and nitrobenzenes was reported for the first time over metal phosphides. Dual active sites, including metal sites for nitro hydrogenation, acid sites for furan alcohol ring-opening determine the catalytic performance. Different from traditional tandem catalysts of Pd/C and HZSM-5 or Amberlyst-15 that suffer from binary competitive adsorption of furan and nitro groups on metal sites, as well as hydroxyl and hydrogenated amino groups on the acidic sites, metal phosphides show unexpected cooperative catalytic properties with the oriented synthesis of pyrroles over NiCoP and tetrahydropyrroles over Ni 2 P. Furthermore, the catalyst displays outstanding stability and recycling performance after 4 runs. This work demonstrates an effective strategy for governing reaction routes by selective activation and shows the powerful synergistic effect of hydrogenation and acid catalysis.
研究领域:
有机化学
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催化化学
✓ 已验证
产品关联
DOI
高影响因子
NEW CARBON MATERIALS
·
2017
·
IF 1.02
Chun-yan Chen,Xiao-ya Guo,Guang-qiang Lu,Christian Marcus Pedersen,Yan Qiao,Xiang-lin Hou,Ying-xiong Wang
Graphene oxide (GO) was used as an efficient and recyclable catalyst for the synthesis of N-substituted pyrrole using a Paal–Knorr condensation reaction between 2,5-hexanedione and aniline. The effects of reaction time, reaction temperature, solvent, catalyst loading and molar ratio of aniline to 2,5-hexanedione on the yield of 2,5-dimethyl-N-phenyl pyrrole were investigated. In situ NMR was used to follow the Paal–Knorr reaction at the molecular level. Results revealed that the oxygen-containing groups of GO, such as sulfonic acid and carboxyl groups, played a key role in this catalytic reaction. Polar protic solvents were favorable for the reaction. The catalytic activity increased with temperature without any side reaction. The GO could be easily recovered and showed remarkable reusability and excellent catalytic performance allowing it to be reused 5 times.
研究领域:
有机化学
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材料科学
·
催化化学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2024
·
IF 3.3
Wei-Wei Zhang,Qiang Sha
An efficient B(C6F5)3-catalyzed multicomponent reaction of 2,3-diketoesters, amines, allenes, and nucleophiles was reported, which afforded 2α-functionalized pyrroles in moderate to good yields. The reaction features low catalyst loading, usage of a small amount of solvent, high atom economy, tunable installation of diverse functional groups at 2α-position, and water being formed as the byproduct. This is the first multicomponent reaction that combines vicinal tricarbonyl compounds with allenes.
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
JOURNAL OF CATALYSIS
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2022
·
IF 8.047
Yamei Lin,Fei Wang,Enxiang Ren,Fuying Zhu,Qiang Zhang,Guo-Ping Lu
The development of novel iron heterogeneous catalysts for organic synthesis is attractive and significant for both academic and industrial applications. A carbon-based iron heterogeneous catalyst (Fe@NSiC) comprising of different iron species including iron atomic single sites (FeN x Si y ), iron silicate and iron nanoparticles (NPs) has been developed. This catalyst exhibits high performance on the solvent-free synthesis of pyrroles from nitroarenes and 2,5-hexanedione via cascade reaction using HCOOH/DBU as the reductant. Si doping can increase Lewis acid sites of the catalyst and the electron density of iron sites, thus promoting the reaction. Furthermore, a set of pyrroles reflecting potential interest from the pharmaceutical perspective are obtained with moderate to excellent yields in this chemistry.
研究领域:
催化
·
有机化学
·
药物化学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）