Bis(cyclopropenium)phosphines: Synthesis, Reactivity, and Applications
| Autor: | Jonathan W. Dube, Manuel Alcarazo, Gerlinde Mehler, Javier Carreras, Alessandro Zanardi, Pawel Linowski |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Steric effects
010405 organic chemistry Ligand Organic Chemistry Substituent Homogeneous catalysis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Toluene Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry Reactivity (chemistry) Solubility |
| Zdroj: | Chemistry - A European Journal. 22:15320-15327 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201601759 |
| Popis: | A straightforward route for the preparation of a set of bis(cyclopropenium)-substituted phosphines is reported. Due to their dicationic nature, these ligands depict an excellent π-acceptor character. The effect of the ligand substituent pattern on the catalytic activity of the metal complexes thereof derived is also studied. Whereas sterically demanding biaryl groups directly attached to the phosphorus atom seem to facilitate elementary steps such as the product release from the catalyst, long chain dialkylamino groups on the cyclopropenium units maximize the catalysts solubility and, thus, allow the use of typical apolar solvents such as toluene. Importantly, all new ligands prepared can be easily handled in air. Finally, the impact of the newly prepared dicationic phosphines in hydroarylation reactions is demonstrated. In particular, their use in the synthesis of several naphtho[1,2-b]furanes and naturally occurring naphthalene derivatives such as Calanquinone C is reported. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|