Catalytic activation of a single C–F bond in trifluoromethyl arenes
| Autor: | Gojko Lalic, Hester Dang, Aaron M. Whittaker |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Trifluoromethyl
Carbon atom 010405 organic chemistry Selective catalytic reduction General Chemistry 010402 general chemistry Photochemistry Highly selective 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis Chemistry chemistry.chemical_compound chemistry Selectivity Direct transformation |
| Zdroj: | Chemical Science |
| ISSN: | 2041-6539 2041-6520 |
| Popis: | Catalytic activation of a single C–F bond in a trifluoromethyl group was used to accomplish highly selective monodefluorination of trifluoromethyl arenes. An investigation of the reaction mechanism suggests the formation of an unexpected intermediate and provides evidence for an unusual reaction pathway responsible for the observed selectivity. Synthetic methods for the direct transformation of ArCF3 to ArCF2R would enable efficient diversification of trifluoromethyl arenes and would be of great utility in medicinal chemistry. Unfortunately, the development of such methods has been hampered by the fundamental properties of C–F bonds, which are exceptionally strong and become stronger with increased fluorination of the carbon atom. Here, we describe a method for the catalytic reduction of ArCF3 to ArCF2H through a highly selective activation of a single C–F bond. Mechanistic studies reveal separate reaction pathways for the formation of ArCF2H and ArCH3 products and point to the formation of an unexpected intermediate as the source of the unusual selectivity for the mono-reduction. |
| Databáze: | OpenAIRE |
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