Synthesis of functionalized tetrahydrofuran derivatives from 2,5-dimethylfuran through cascade reactions

Abstract

A three-step strategy is proposed for the functionalization of the methyl group of 2,5-dimethylfuran, encompassing the ring opening of 2,5-dimethylfuran to 2,5-hexanedione, its further aldol condensation with aldehydes, and hydrogenation–cyclization of the condensation intermediate to generate alkylated tetrahydrofuran. Active and selective catalysts could be identified for the aldol condensation and hydrogenation–cyclization reactions.