Copper-mediated tetrafluoroethylation of unsaturated organotrifluoroborates <i>via</i> generation of the HCF <sub>2</sub> CF <sub>2</sub> -radical from zinc 1,1,2,2-tetrafluoroethanesulfinate
A copper-mediated synthetic method for the incorporation of the 1,1,2,2-tetrafluoroethyl (CF<sub>2</sub>CF<sub>2</sub>H) group into unsaturated potassium organotrifluoroborate systems using the zinc 1,1,2,2-tetrafluoroethanesulfinate reagent has been developed. The HCF<sub>2</sub>CF<sub>2</sub>-radical, derived <i>in situ</i> from (HCF<sub>2</sub>CF<sub>2</sub>SO<sub>2</sub>)<sub>2</sub>Zn using TBHP as an oxidant, combines with a copper-catalyst to promote the replacement of the BF<sub>3</sub>K group on alkenes and alkynes. The reactions are carried out under ambient air, using mild and practical conditions. The method provides access to tetrafluoroethylated alkene and alkyne products in moderate to good yields.
Authors
- Md Nirshad Alam (ORCID: https://orcid.org/0000-0003-1076-7013)
- Takahiro Umemoto (ORCID: https://orcid.org/0000-0002-5684-6350)
- Satyajit Majumder (ORCID: https://orcid.org/0009-0001-0454-8415)
- William R. Dolbier (ORCID: https://orcid.org/0000-0003-2067-8137)
Institutions
- University of Florida (US)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01033k
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- University of Florida
- National Institutes of Health