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Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent
| Content Provider | Hyper Articles en Ligne (HAL) |
|---|---|
| Author | Kalim, Jorna Duhail, Thibaut Pietrasiak, Ewa Anselmi, Elsa Magnier, Emmanuel Togni, Antonio |
| Abstract | The direct trifluoromethylation of a variety of aliphatic alcohols using a hypervalent iodosulfoximine reagent afforded the corresponding ethers in moderate to good yields (14–72 %). Primary, secondary, and even tertiary alcohols, including examples derived from natural products, underwent this transformation in the presence of catalytic amounts of zinc bis(triflimide). Typical reaction conditions involved a neat mixture of 6.0 equivalents of the alcohol with 1.0 equivalent of the reagent, with the majority of reactions complete within 2 h with 2.5 mol % of the Lewis acid catalyst. Furthermore, experimental evidence was provided that the C−O bond-forming process occurred via the coordination of the alcohol to the iodine atom and subsequent reductive elimination. |
| Related Links | https://hal.science/hal-03121267/file/Manuscript_chem.202005104.pdf |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| DOI | 10.1002/chem.202005104 |
| Journal | Chemistry - A European Journal |
| Language | English |
| Publisher | HAL CCSD Wiley-VCH Verlag |
| Publisher Date | 2020-11-26 |
| Access Restriction | Open |
| Subject Keyword | hypervalent iodine sulfoximines trifluoromethylation organofluorine compounds trifluoromethylethers Chemical Sciences |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis Chemical Engineering |