Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives
| Autor: | Raffaella Mancuso, Carla Carfagna, Bartolo Gabriele, Antonio Palumbo Piccionello, Nicola Della Ca, Rossana Miliè, Diego Olivieri |
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| Přispěvatelé: | Mancuso R., Milie R., Palumbo Piccionello A., Olivieri D., Della Ca N., Carfagna C., Gabriele B. |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Organic Chemistry chemistry.chemical_element Ionic Liquids Carbonylation Settore CHIM/06 - Chimica Organica 010402 general chemistry 01 natural sciences Palladium Cyclization 0104 chemical sciences Catalysis chemistry.chemical_compound Ionic liquids palladium catalyst benzofuran chemistry Ionic liquid Organic chemistry Phenols |
| Popis: | A catalytic carbonylative double cyclization method for the synthesis of furo[3,4-b]benzofuran-1(3H)-ones is reported. It is based on the reaction between readily available 2-(3-hydroxy-1-yn-1-yl)phenols, CO, and oxygen carried out in the presence of catalytic amounts of PdI2 (1 mol %) in conjunction with KI (20 mol %) and 2 equiv of diisopropylethylamine at 80 degrees C for 24 h under 30 atm of a 1:4 mixture of CO-air. Interestingly, the process was not selective when carried out in classical organic non-nucleophilic solvents (such as MeCN or DME), leading to a mixture of the benzofurofuranone derivative and the benzofuran ensuing from simple cycloisomerization, whereas it turned out chemoselective toward the formation of the double cyclization compound in BmimBF(4) as the reaction medium. Moreover, the ionic liquid solvent containing the catalyst could be easily recycled several times without appreciable loss of activity. |
| Databáze: | OpenAIRE |
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