A more efficient synthetic process of N-arylphthalimides in ionic liquid [bmim][BF4]

Chen, Dong Chu; Ye, Hong Qi; Wu, Hao

doi:10.1016/j.catcom.2006.12.024

Cited by 20 publications

(5 citation statements)

References 16 publications

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“…1 H NMR (400 MHz, CDCl 3 ): δ 7.96 (dd, J = 5.6, 3.2 Hz, 2H), 7.80 (dd, J = 5.6, 3.2 Hz, 2H), 7.59–7.55 (m, 1H), 7.46–7.38 (m, 2H), 7.37–7.35 (m, 1H) ppm. The spectral data match those previously reported …”

Section: Methodssupporting

confidence: 89%

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Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

et al. 2019

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We report on cyclic imides as weak directing groups for selective mono-hydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp 2)-H bond enabling 5-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp 2)-H bond via a larger 6-membered ruthenacycle intermediates. Furthermore, mono-hydroxylated products were exclusively obtained (even in the presence of over-stoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate co-planar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.  ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publications website at DOI: XXX. Screening of reaction conditions, computational details and NMR spectra (PDF) Crystallographic data for 2b (CCDC-187307, CIF) Crystallographic data for 2d (CCDC-1873708, CIF)  AUTHOR INFORMATION

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Section: Methodssupporting

confidence: 89%

“…The spectral data match those previously reported. 40 N-(2-Biphenyl)phthalimide (1af). Prepared according to method A starting from 2-chloroaniline in 50% isolated yield (878 mg).…”

Section: ■ Conclusionmentioning

confidence: 99%

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

et al. 2019

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“…The areas of application include catalysis [2], extraction [3,4], synthesis [5], dissolution [6,7], nuclear industry [8], food science [9], etc. Non-volatility and nonflammability are their common characteristics giving them an advantageous edge in various applications.…”

Section: Introductionmentioning

confidence: 99%

Effect of ionic liquid on the toxicity of pesticide to Vibrio-qinghaiensis sp.-Q67

Zhang

Liu

2009

Journal of Hazardous Materials

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“…More recently, Chu and coworkers have also reported [157] an improved and efficient protocol for synthesis of N-aryl phthalimides 143, through the N-alkylation of phthalic anhydride 142 with aromatic amines 10 using ionic liquid [Bmim] …”

Section: N-aryl/alkyl Phthalimidesmentioning

confidence: 99%

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

Chaturvedi

2011

COS

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Ionic liquids have been emerging as a versatile class of green solvents with many projected advantages compared with conventional media. They have been described as "designer solvents" whose properties such as solubility, density, refractive index, and viscosity can be adjusted to suit requirements simply by making changes to the structure of either anion or cation or both. In organic synthesis, ionic liquids have been extensively used for the variety of synthetic transformations. Recently, plethoras of nitrogen heterocycles have been synthesized using variety of structurally diverse ionic liquids. In the present review, I would account the synthesis of various kinds of nitrogen heterocycles using variety of ionic liquids from the beginning to the recent reports.

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A more efficient synthetic process of N-arylphthalimides in ionic liquid [bmim][BF4]

Cited by 20 publications

References 16 publications

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

Ru-Catalyzed Selective C–H Bond Hydroxylation of Cyclic Imides

Effect of ionic liquid on the toxicity of pesticide to Vibrio-qinghaiensis sp.-Q67

Ionic Liquids: A Class of Versatile Green Reaction Media for the Syntheses of Nitrogen Heterocycles

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