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

Antonio Palumbo Piccionello, Nicola Della Ca, Carla Carfagna, Diego Olivieri, Rossana Miliè, Bartolo Gabriele, Raffaella Mancuso

Risultato della ricerca: Article

4 Citazioni (Scopus)

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.
Lingua originaleEnglish
pagine (da-a)7303-7311
Numero di pagine9
RivistaJournal of Organic Chemistry
Volume84
Stato di pubblicazionePublished - 2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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