Johari, Suzaimi and Johan, Mohd Rafie and Ghaffari Khaligh, Nader (2024) Impact of a homogeneous hydrogen bond catalysis for the ethyl (hetero)arylidene cyanoacetate preparation in the presence of TMDP. Research on Chemical Intermediates, 50 (12). pp. 5725-5753. ISSN 0922-6168, DOI https://doi.org/10.1007/s11164-024-05434-y.
Full text not available from this repository.Abstract
The synthesis of ethyl (hetero)arylidene cyanoacetates, valuable intermediates in organic chemistry, has been investigated using several commercially available and synthetic nitrogen-based organocatalysts. 4,4 `-Trimethylenedipiperidine (TMDP) was chosen as an efficient organocatalyst regarding short reaction times, excellent yield with a conversion of 100%, and high selectivity. The pure products could be isolated and devoid of a costly workup. The residue could be directly reused for the next catalytic run. Encouragingly, TMDP exhibited chemical stability and high recyclability in five subsequent runs without a significant loss in catalytic activity. Scale-up experiments also demonstrate the current strategy's promising industrial application. Mechanistic studies were conducted to provide insights into the reaction pathways and possible interaction/reaction between organocatalyst and each reactant through performing control experiments and studying FTIR in neat state and NMR spectra in aprotic and protic deuterated solvents. The developed metal-free and halogen-free catalytic strategy offers cost-effectiveness, low toxicity, and enhanced sustainability.
| Item Type: | Article |
|---|---|
| Funders: | Nippon Sheet Glass Foundation for Materials Science and Engineering |
| Uncontrolled Keywords: | Homogeneous catalysis; Nitrogen heterocycles; Reaction mechanisms; Hydrogen boding; Green chemistry |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Deputy Vice Chancellor (Research & Innovation) Office > Nanotechnology & Catalysis Research Centre |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 24 Feb 2025 01:54 |
| Last Modified: | 24 Feb 2025 01:54 |
| URI: | http://eprints.um.edu.my/id/eprint/47300 |
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