Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds
A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the successful derivatizati...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.263 |
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| author | Radell Echemendía Carlee A. Montgomery Fabio Cuzzucoli Antonio C. B. Burtoloso Graham K. Murphy |
| author_facet | Radell Echemendía Carlee A. Montgomery Fabio Cuzzucoli Antonio C. B. Burtoloso Graham K. Murphy |
| author_sort | Radell Echemendía |
| collection | DOAJ |
| description | A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the successful derivatization of sulfoxonium ylides with trifluoroethyl or tetrafluoropropyl groups, and provides valuable insights into the scope and limitations of this approach. Nineteen examples have been prepared (45–92% yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Finally, DFT calculations provided insights about the mechanism of this transformation, which strongly suggest that an SN2 reaction is operative. |
| format | Article |
| id | doaj-art-5445072e3a6541c9ae94144b65adb9fc |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-5445072e3a6541c9ae94144b65adb9fc2025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013182319010.3762/bjoc.20.2631860-5397-20-263Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compoundsRadell Echemendía0Carlee A. Montgomery1Fabio Cuzzucoli2Antonio C. B. Burtoloso3Graham K. Murphy4São Carlos Institute of Chemistry, University of São Paulo, 13560-970, São Carlos, SP, Brazil Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, Ontario, Canada Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, Ontario, Canada São Carlos Institute of Chemistry, University of São Paulo, 13560-970, São Carlos, SP, Brazil Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, Ontario, Canada A novel study on the hypervalent iodine-mediated polyfluoroalkylation of sulfoxonium ylides was developed. Sulfoxonium ylides, known for their versatility and stability, are promising substrates for numerous transformations in synthetic chemistry. This report demonstrates the successful derivatization of sulfoxonium ylides with trifluoroethyl or tetrafluoropropyl groups, and provides valuable insights into the scope and limitations of this approach. Nineteen examples have been prepared (45–92% yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Finally, DFT calculations provided insights about the mechanism of this transformation, which strongly suggest that an SN2 reaction is operative.https://doi.org/10.3762/bjoc.20.263alkylationdft calculationsfluorine chemistryhypervalent iodinesulfoxonium ylidesulphur ylides |
| spellingShingle | Radell Echemendía Carlee A. Montgomery Fabio Cuzzucoli Antonio C. B. Burtoloso Graham K. Murphy Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds Beilstein Journal of Organic Chemistry alkylation dft calculations fluorine chemistry hypervalent iodine sulfoxonium ylide sulphur ylides |
| title | Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| title_full | Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| title_fullStr | Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| title_full_unstemmed | Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| title_short | Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| title_sort | direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds |
| topic | alkylation dft calculations fluorine chemistry hypervalent iodine sulfoxonium ylide sulphur ylides |
| url | https://doi.org/10.3762/bjoc.20.263 |
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