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Catalytic HF Shuttling between Fluoroalkanes and Alkynes**.
- Source :
-
Angewandte Chemie International Edition . 1/25/2024, Vol. 63 Issue 5, p1-6. 6p. - Publication Year :
- 2024
-
Abstract
- In this paper, we report BF3 ⋅ OEt2 as a catalyst to shuttle equivalents of HF from a fluoroalkane to an alkyne. Reactions of terminal and internal aliphatic alkynes led to formation of difluoroalkane products, while diarylalkynes can be selectively converted into fluoroalkenes. The method tolerates numerous sensitive functional groups including halogen, protected amine, ester and thiophene substituents. Mechanistic studies (DFT, probe experiments) suggest the catalyst is involved in both the defluorination and fluorination steps, with BF3 acting as a Lewis acid and OEt2 a weak Lewis base that mediates proton transfer. In certain cases, the interconversion of fluoroalkene and difluoroalkane products was found to be reversible. The new catalytic system was applied to demonstrate proof‐of‐concept recycling of poly(vinylidene difluoride). [ABSTRACT FROM AUTHOR]
- Subjects :
- *LEWIS bases
*LEWIS acids
*FLUORINATION
*HALOGENS
*FUNCTIONAL groups
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 63
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 174912193
- Full Text :
- https://doi.org/10.1002/anie.202317550