Pchenushay, Darina (2024) UNDERSTANDING COPPER MEDIATED C-N CROSS-COUPLING REACTION BETWEEN BROMO-ANILINE AND PROPARGYLIC ALCOHOL. Master's Internship Report, Chemistry.
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Abstract
The field of cross-coupling reactions is a growing field, as cross-coupling reactions are essential components in organic synthesis. While various catalysts can achieve cross-coupling reactions, expensive catalysts such as Ru or Pd can often be used. In recent years, copper has been utilized as a more sustainable alternative for catalysts in various reactions. Previous works on the C-N cross-coupling reaction of bromoaniline and propargylic alcohol, with copper as an active catalyst, have not been fully understood. This includes the reaction's mechanism and which side product is formed. This work focuses on a better understanding of such a reaction. Firstly, the structure of the by-product of this cross-coupling was determined through various NMR techniques. Secondly, the optimum conditions for both products were found by testing various parameters, such as solvent, temperature, ligand, and more. The results suggest that solvent effect and temperature have the biggest influence on the selectivity of the product. A maximum of 73% NMR yield was obtained for the cross-coupling product. A fully cyclized spiro product was obtained with a maximum of 34% NMR yield. Lastly, a catalytic cycle was proposed based on the effect of various alterations. Nonetheless, more mechanistic studies need to be done to unravel all the details of the mechanism of this reaction.
| Item Type: | Thesis (Master's Internship Report) |
|---|---|
| Supervisor name: | Minnaard, A.J. and Browne, W.R. |
| Degree programme: | Chemistry |
| Thesis type: | Master's Internship Report |
| Language: | English |
| Date Deposited: | 29 Apr 2024 10:27 |
| Last Modified: | 29 Apr 2024 10:27 |
| URI: | https://fse.studenttheses.ub.rug.nl/id/eprint/32349 |
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