Herein we report the use of Rhodiasolv© Polarclean as a novel polar aprotic solvent for the synthesis of decorated heterocycles via dipolar cycloaddition (isooxazoles) or intramolecular C–H functionalization processes (benzo-fused chromenes). The use of Polarclean allowed to isolate the final products in good yields by simple solid filtration or liquid-liquid phase separation, avoiding the need for chromatographic purification. Moreover, since in the synthesis of benzo-fused chromenes, themetal catalyst is retained in Polarclean, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without any apparent loss in efficiency. Thismethodology is associated with a limited waste production. These results extend the applicability of Polarclean as a promising reaction medium for the replacement of toxic petrol-based solvent.

Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds

Francesco Ferlin;Lorenzo Luciani;Oriana Piermatti;Stefano Santoro;Luigi Vaccaro
2019

Abstract

Herein we report the use of Rhodiasolv© Polarclean as a novel polar aprotic solvent for the synthesis of decorated heterocycles via dipolar cycloaddition (isooxazoles) or intramolecular C–H functionalization processes (benzo-fused chromenes). The use of Polarclean allowed to isolate the final products in good yields by simple solid filtration or liquid-liquid phase separation, avoiding the need for chromatographic purification. Moreover, since in the synthesis of benzo-fused chromenes, themetal catalyst is retained in Polarclean, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without any apparent loss in efficiency. Thismethodology is associated with a limited waste production. These results extend the applicability of Polarclean as a promising reaction medium for the replacement of toxic petrol-based solvent.
2019
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/1447978
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