A method for the preparation of air stable difluoroboryl acrylamides is reported. In contrast to the ubiquitous organotrifluoroborate salts, difluoroboryl acrylamides are relatively nonpolar and are readily purified by silica gel chromatography. Difluoroboryl acrylamides serve as efficient substrates in cross-coupling reactions to afford the corresponding trisubstituted acrylamides in good to excellent yields. The utility of the difluoroboryl group in various chemical transformations is presented. / A new method for the formation of a unique difluorinated boron-based functional group is reported. In contrast to the commonly observed trifluoronated boron species, the difluoroboryl species is relatively nonpolar, which allows for these compounds to be purified by silica gel chromatography, a convenient method for purification of compounds. Similarly to trifluoroborate salts, difluoroboryl species are capable of undergoing cross-coupling reactions, which form carbon-carbon bonds, in good to excellent yields. Additional examples of chemical reactions using difluoroboryl acrylamides are also presented.
| Identifer | oai:union.ndltd.org:VTETD/oai:vtechworks.lib.vt.edu:10919/95059 |
| Date | 09 1900 |
| Creators | Medici, Eric |
| Contributors | Chemistry, Santos, Webster L., Carlier, Paul R., Matson, John B., Tanko, James M. |
| Publisher | Virginia Tech |
| Source Sets | Virginia Tech Theses and Dissertation |
| Language | en_US |
| Detected Language | English |
| Type | Thesis |
| Format | ETD, application/pdf |
| Rights | Creative Commons Attribution 4.0 International, http://creativecommons.org/licenses/by/4.0/ |
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