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Synthesis 1996; 1996(3): 388-392
DOI: 10.1055/s-1996-4218
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Synthesis of 2,5-Diaryl-3-halofurans via Regioselective Ring Cleavage of Aryl 3-Aryl-2,2-dihalocyclopropyl Ketones

Yoo Tanabe* , Ken-ichi Wakimura, Yoshinori Nishii, Yukari Muroya
  • *School of Science, Kwansei Gakuin University, 1-1-155 Uegahara, Nishinomiya, Hyogo 662, Japan, Fax +81(798)510914
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Publication Date:
31 December 2000 (online)

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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.

halofuran - regioselective - gem-dihalocyclopropane - lithiation - tetrasubstituted furan