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Role of Pyridine Nitrogen in Palladium-Catalyzed Imine Hydrolysis: A Case Study of (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine
| Content Provider | Semantic Scholar |
|---|---|
| Author | Ahmad, Gulraiz Rasool, Nasir Rizwan, Komal Altaf, Ataf Ali Rashid, Umer Hussein, Mohd Zobir Mahmood, Tariq Ayub, Khurshid |
| Copyright Year | 2019 |
| Abstract | In the present study, 4-methylpyridin-2-amine was reacted with 3-bromothiophene-2-carbaldehyde and the Schiff base (E)-1-(3-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine was obtained in a 79% yield. Coupling of the Schiff base with aryl/het-aryl boronic acids under Suzuki coupling reaction conditions, using Pd(PPh3)4 as catalyst, yielded products with the hydrolysis of the imine linkages (5a-5k, 6a-6h) in good to moderate yields. To gain mechanistic insight into the transition metal-catalyzed hydrolysis of the compounds, density functional theory (DFT) calculations were performed. The theoretical calculations strongly supported the experiment and provided an insight into the transition metal-catalyzed hydrolysis of imines. |
| File Format | PDF HTM / HTML |
| DOI | 10.3390/molecules24142609 |
| PubMed reference number | 31319634 |
| Journal | Medline |
| Volume Number | 24 |
| Alternate Webpage(s) | https://res.mdpi.com/d_attachment/molecules/molecules-24-02609/article_deploy/molecules-24-02609-v2.pdf |
| Alternate Webpage(s) | https://doi.org/10.3390/molecules24142609 |
| Journal | Molecules |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
