Palladium-Catalyzed Cross-Coupling of Furfuryl Alcohols with Arylboronic Acids via Aromatization-Driven Carbon-Carbon Bond Cleavage to Synthesize 5-Arylfurfuryl Alcohols and 2,5-Diaryl Furans

摘要

Herein we report a protocol for novel palladium-catalyzed cross-coupling reactions of sustainably produced primary furfuryl alcohols with arylboronic acids to deliver 5-arylfurfuryl alcohols and 2,5-diaryl furans. Hammett plot analysis suggested that the reaction mechanism involved aromatization-driven cleavage of the carbon-carbon bond of a furan oxonium ion intermediate. This protocol provides a simple, practical way to transform 5-hydroxymethylfurfural into useful compounds.