1 Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke Street West, Montreal QC H4B 1R6, Canada.
2 Centre in Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal QC H3A 2K6, Canada.

Synthesis of 2,5-Diaryl Nonsymmetric Furans C6-Platform Chemicals via Catalytic Conversion of Biomass and the Formal Synthesis of Dantrolene.

J Org Chem. 2020 Nov 30; :

Authors: Chacón-Huete F, Lasso JD, Szavay P, Covone J, Forgione P

Abstract

Biomass-derived commodity chemical 5-hydroxymethyl furfural is an underutilized C6-platform chemical derived from cellulose that is ideal to prepare next-generation value-added products. We have developed an efficient synthetic strategy to access 2,5-diaryl nonsymmetric furans from 5-hydroxymethyl furfural utilizing decarboxylative cross-couplings. A key finding was that the presence of the hydroxymethyl handle enhances the yields of the palladium-catalyzed decarboxylative cross-coupling reaction. The method provides access to a broad-range nonsymmetric 2,5-diaryl furans where each arene can be systematically introduced as required. Additionally, this green synthetic strategy was employed for a formal synthesis of the muscle relaxant Dantrolene in excellent yields.

PMID: 33253575 [PubMed - as supplied by publisher]