Divergent Synthesis of Tetrafluoroethylene-Containing Tetrahydrofuran (THF) and Dihydropyran (DHP) Derivatives
A divergent synthetic methodology for tetrafluoroethylene (CF<sub>2</sub>CF<sub>2</sub>)-containing tetrahydrofurans (THFs) and dihydropyrans (DHPs), employing 4-bromo-2,2,3,3-tetrafluoro-4-penten-1-ol derivatives as common synthetic intermediates, has been developed. Mechanistic studies indicate that the reaction proceeds chemoselectively, either via copper-catalyzed Ullmann-type intramolecular <i>O</i>-vinylation or through tandem CF<sub>2</sub>CF<sub>2</sub> group-promoted β-elimination followed by 6-<i>endo</i>-dig cycloisomerization. Further investigations demonstrate that both cyclic ethers can be diastereoselectively transformed into a wide range of CF<sub>2</sub>CF<sub>2</sub>-containing <i>C</i>-glycoside derivatives.
Authors
- Motohiro Yasui (ORCID: https://orcid.org/0000-0001-9324-3463)
- Suguru Morishitabara
- Shigeyuki Yamada (ORCID: https://orcid.org/0000-0002-6379-0447)
- Tsutomu Konno (ORCID: https://orcid.org/0000-0002-5146-9840)
- K. R. Nakamura (ORCID: https://orcid.org/0000-0001-7012-7355)
- Shota Kageyama
- Masato Morita (ORCID: https://orcid.org/0009-0009-9372-3489)
Institutions
- Kyoto Institute of Technology (JP)
- Ibaraki University (JP)
- Hitachi (Japan) (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c03889
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00