Chelation-Mediated Palladium(II)-Catalyzed Domino Heck−Mizoroki/Suzuki−Miyaura Reactions Using Arylboronic Acids: Increasing Scope and Mechanistic Understanding
| Autor: | Alejandro Trejos, Samir Yahiaoui, Mats Larhed, Ashkan Fardost |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Vinyl Compounds
chemistry.chemical_element Electrons Ether Catalysis Reductive elimination chemistry.chemical_compound Transmetalation Cascade reaction Coordination Complexes Benzoquinones Organic chemistry Chelating Agents Olefin fiber Ligand Organic Chemistry Green Chemistry Technology Stereoisomerism Boronic Acids Combinatorial chemistry chemistry Oxidation-Reduction Palladium Ethers |
| Zdroj: | The Journal of Organic Chemistry. 76:2433-2438 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo1018188 |
| Popis: | A palladium(II)-catalyzed Heck-Mizoroki/Suzuki-Miyaura domino reaction involving metal coordinating dimethylaminoethyl vinyl ethers and a number of electron-rich and electron-deficient arylboronic acids has been developed. Through variation of the temperature and the concentration of the p-benzoquinone (p-Bq) ligand/reoxidant, conditions for the robust and convenient one-pot generation of diarylated-saturated ethers were identified. With the aid of coordination of the dimethylamino group to the arylpalladium intermediate, the otherwise predominant formation of the β-arylated olefin could be reversed. A reaction route involving a chelation-controlled carbopalladation, providing a p-Bq stabilized six-membered palladacycle, followed by transmetalation and reductive elimination is suggested to explain the selective formation of saturated diarylated ether products. |
| Databáze: | OpenAIRE |
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