4.6 Article

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

Journal

FRONTIERS IN CHEMISTRY
Volume 6, Issue -, Pages -

Publisher

FRONTIERS MEDIA SA
DOI: 10.3389/fchem.2018.00659

Keywords

heterocycles; green-synthesis; isoxazoles; triazoles; C-H activation

Funding

  1. MIUR Dipartimenti di Eccellenza-2018-2022: AMIS

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Herein we report the use of Rhodiasolv(C) 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, the metal catalyst is retained in Polarclean, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without any apparent loss in efficiency. This methodology 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.

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