| Autor: |
Sedikides AT; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom., Lennox AJJ; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom. |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2024 Jun 12; Vol. 146 (23), pp. 15672-15680. Date of Electronic Publication: 2024 Jun 03. |
| DOI: |
10.1021/jacs.4c03826 |
| Abstrakt: |
Monofluoroalkenes are stable and lipophilic amide bioisosteres used in medicinal chemistry. However, efficient and stereoselective methods for synthesizing Z -monofluoroalkenes are underdeveloped. We envisage (Z)- β-fluoro-vinyl iodonium salts ( Z -FVIs) as coupling partners for the diverse and stereoselective synthesis of Z -monofluoroalkenes. Disclosed herein is the development and application of a silver(I)-catalyzed process for accessing a broad scope of ( Z )-FVIs with exclusive Z -stereoselectivity and regioselectivity from alkynes in a single step. Experimental and computational studies provide insight into the mechanism of the catalytic cycle and the role of the silver(I) catalyst, and the reactivity of ( Z )-FVIs is explored through several stereospecific derivatizations. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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