Journal Article Benzoxazole-Directed Halogen Dance of Bromofuran

Miyagawa, Naoki  ,  Murase, Yuki  ,  Okano, Kentaro  ,  Mori, Atsunori

28 ( 9 )  , pp.1106 - 1110 , 2017-06 , Thieme Publishing
A halogen dance of a benzoxazole-conjugated bromofuran derived from furfural is described. The reaction proceeds through a benzoxazole-directed lithiation to provide the α-lithiofuran, which is subjected to Negishi coupling to give α-arylated benzoxazole-conjugated furan derivatives. The synthetic utility of the reaction was demonstrated by transformation of the residual bromo group into a side chain bearing a siloxane moiety, which resulted in a significant improvement in solubility in organic solvents.

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