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Synthesis of 5,5′‐Diformyl‐2,2′‐difuran from 2‐Furfural by Photochemical Aryl Coupling
Author(s) -
Taljaard Benjamin,
Burger Gregory J.
Publication year - 2002
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 - 10.1002/1615-4169(200212)344:10<1111::aid-adsc1111>3.0.co;2-0
Subject(s) - chemistry , furfural , acetonitrile , photochemistry , aryl , excimer , intermolecular force , coupling (piping) , organic chemistry , fluorescence , alkyl , catalysis , molecule , mechanical engineering , physics , quantum mechanics , engineering
The synthesis of 5,5′‐diformyl‐2,2′‐difuran (IUPAC name: [2,2′‐bifuryl]‐5,5′‐dicarbaldehyde) in good yields by the intermolecular coupling of 2‐furfural and 5‐bromo‐2‐furfural has been achieved. Optimum yields were obtained when mixtures of the substrates in acetonitrile were treated with polyvinylpyridine powder (Reillex 402), and irradiated with UV light through a quartz filter. Low yields of coupling product were obtained in the absence of this base or if hydrocarbon solvents were used. A mechanistic pathway involving a transient exciplex intermediate has been proposed.