Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates
DOI: 10.14469/hpc/12218 Metadata
Created: 2023-01-28 09:55
Last modified: 2024-11-12 12:55
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Andrew Whiting Co-author: Carla Alamillo-Ferrer Co-author: Dejan-Kresimir Bucar Co-author: Jordi Bures Co-author: Richard Procter Co-author: Tom Sheppard Co-author: Usman Shabbir
Description
The catalytic activity of different classes of boron catalysts was studied in amidation reactions with 4-phenylbutylamine/benzoic acid, and with 2-aminopyridine/phenylacetic acid. Whilst a simple boronic acid catalyst showed high catalytic activity with the former substrates, it was completely inactive in the latter reaction. In contrast, a borate ester catalyst was able to mediate the amidation of both substrate pairs with moderate activity. By screening a range of borate esters we were able to identify a novel borate catalyst that shows high reactivity with a range of challenging carboxylic acids/amine pairs, enabling catalystic amidation reactions to be achieved effectively with these industrially relevant compounds. The reactions can be perfomed on multigram scale with high levels of efficiency and in situ catalyst generation from commercially available reagents renders the process readily accessible for everyday laboratory use. Further experiments showed that the deactivating effect of 2-aminopyridine was due to its ability to stabilise catalytically inactive boroxines.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/14832 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates. Kinetic Data |
| 10.14469/hpc/14822 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates. Supporting Information |
| 10.14469/hpc/14634 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates. Computational data |
| 10.14469/hpc/14694 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates. Crystal structure data |
| 10.14469/hpc/14635 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates. NMR data |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.26434/chemrxiv-2024-b1lz5 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates, ChexRxiv preprint. |
| isReferencedBy | 10.26434/chemrxiv-2024-b1lz5 | Borate-Catalysed Direct Amidation Reactions of Coordinating Substrates, ChexRxiv preprint. |