Lewis Acid Assisted Nickel‐Catalyzed Cross‐Coupling of Aryl Methyl Ethers by C−O Bond‐Cleaving Alkylation: Prevention of Undesired β‐Hydride Elimination
| Autor: | Lin Guo, Magnus Rueping, Chien-Chi Hsiao, Franziska Schoenebeck, Xiangqian Liu, Matthias Leiendecker, Indrek Kalvet |
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| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Hydride Aryl General Chemistry Alkylation 010402 general chemistry Anisole 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Organic chemistry Lewis acids and bases Alkyl |
| Zdroj: | Angewandte Chemie International Edition. 55:6093-6098 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201510497 |
| Popis: | In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C-O bond-cleaving alkylation, for the first time without the limiting β-hydride elimination. This new nickel-catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process. |
| Databáze: | OpenAIRE |
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