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.

Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives / Mancuso, R.; Milie, R.; Palumbo Piccionello, A.; Olivieri, D.; Della Ca, N.; Carfagna, C.; Gabriele, B.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 84:11(2019), pp. 7303-7311. [10.1021/acs.joc.9b00952]

Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives

Della Ca N.;
2019

Abstract

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.
Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives / Mancuso, R.; Milie, R.; Palumbo Piccionello, A.; Olivieri, D.; Della Ca, N.; Carfagna, C.; Gabriele, B.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 84:11(2019), pp. 7303-7311. [10.1021/acs.joc.9b00952]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2866824
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