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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
Author(s) -
Huang Guanghao,
Yin Biaolin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900799
Subject(s) - chemistry , aromatization , furan , carbon–carbon bond , furfuryl alcohol , oxonium ion , bond cleavage , palladium , organic chemistry , catalysis , carbon fibers , ion , composite material , materials science , composite number
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.