AI Article Synopsis
- The authors present a new method for creating mono- and polyfluoroepoxides using various electrophiles and fluoroalkyl anion equivalents.
- The process involves forming α-fluoro alkoxides that can close into rings when heated, leading to 16 different products showcasing the method's versatility.
- These fluorinated compounds allow for further chemical modifications, including migrating fluoride ions and adding bioactive groups, making them useful for developing new materials or pharmaceuticals.
Article Abstract
We outline a new synthetic method to prepare mono- and polyfluoroepoxides from a diverse pool of electrophiles (ketones, acyl chlorides, esters) and fluoroalkyl anion equivalents. The initially formed α-fluoro alkoxides undergo subsequent intramolecular ring closure when heated. We demonstrated the versatility of the method through the isolation of 16 mono- and polyfluoroepoxide products. These compounds provide unique entry points for further diversification via either fluoride migration coupled with ring opening, or defluorinative functionalization reactions, the latter of which can be used as a late-stage method to install select bioactive moieties. The reaction sequences described herein provide a pathway to functionalize the commonly observed products formed from 1,2-addition into carbonyl electrophiles.
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| http://dx.doi.org/10.1002/chem.202203578 | DOI Listing |
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