Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid bioisosteres
Methods for formal bromo-trifluoromethoxylation and bromo-pentafluorosulfanoxylation of [1.1.0]bicyclobutanes using AgOCF<sub>3</sub> or AgOSF<sub>5</sub> and 1,3-dibromo-5,5-dimethylhydantoin are disclosed. These represent complementary strategies to the syntheses of SF<sub>5</sub>- and CF<sub>3</sub>SF<sub>4</sub>-containing cyclobutanes previously reported from our laboratory, ultimately enabling comparative structural studies and <i>in vitro</i> ADME profiling for various fluorinated cyclobutanes.
Authors
- Yannick Kraemer (ORCID: https://orcid.org/0000-0002-2136-7253)
- Cody Ross Pitts (ORCID: https://orcid.org/0000-0003-1047-8924)
- Alexander M. Stephens (ORCID: https://orcid.org/0000-0002-4952-0256)
- Lauren M. Holder (ORCID: https://orcid.org/0000-0001-8585-8169)
- Connor P. McLoughlin (ORCID: https://orcid.org/0000-0002-4707-1135)
- James C. Fettinger (ORCID: https://orcid.org/0000-0002-6428-4909)
- Jón Atiba Buldt (ORCID: https://orcid.org/0009-0005-4900-0479)
- Andrew Young (ORCID: https://orcid.org/0000-0002-9019-128X)
Institutions
- NovaBay Pharmaceuticals (United States) (US)
- University of California, Davis (US)
Publication Details
- Journal
- Chemical Communications
- Published
- 2024-12-19
- DOI
- https://doi.org/10.1039/d4cc06616b
- Citations
- 16
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 3.33