Autocatalytic Friedel–Crafts Reactions of Tertiary Aliphatic Fluorides Initiated by B(C6F5)3·H2O
| Autor: | Joseph Moran, Marian Dryzhakov |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry General Chemistry Carbocation 010402 general chemistry 01 natural sciences Catalysis 3. Good health 0104 chemical sciences Autocatalysis Polymer chemistry Single bond Organic chemistry Lewis acids and bases Brønsted–Lowry acid–base theory Friedel–Crafts reaction Alkyl |
| Zdroj: | ACS Catalysis. 6:3670-3673 |
| ISSN: | 2155-5435 |
| Popis: | The C–F bond is the strongest single bond to carbon, constituting an intrinsic challenge for selective catalytic activation in the presence of other functional groups. Existing methods for the activation of tertiary aliphatic fluorides involve stoichiometric abstraction with fluorophilic Lewis acids or by Lewis-acid-catalyzed trapping with Si reagents. Herein, we describe a B(C6F5)3·H2O-catalyzed Friedel–Crafts reaction of tertiary alkyl fluorides that proceeds rapidly at room temperature without trapping reagents. The method is completely selective for F– over traditionally better leaving groups and displays an autocatalytic kinetic profile. |
| Databáze: | OpenAIRE |
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