Synthesis of 2,5-diaryl-3-halofurans via regioselective ring cleavage of aryl 3-aryl-2,2-dihalocyclopropyl ketones

Article abstract of DOI:10.1055/s-1996-4218

Several aryl 3-aryl-2,2-dihalocyclopropyl ketones were converted to 2,5-diaryl-3-halofurans in the presence of aluminum chloride via regioselective gem-dihalocyclopropane ring-cleavage. Friedel-Crafts acylation of substituted benzenes with 3-aryl-2,2-dihalocyclopropanecarbonyl chlorides followed by this furan formation also proceeded in a one-pot manner. For functionalization, bromine on a furan ring was easily replaced by methyl and carboxyl groups; lithiation using butyllithium followed by the treatment with iodomethane and carbon dioxide, respectively.