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Wednesday, 19 November 2008 00:00

17. Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans

Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans, Márton Csékei, Zoltán Novák, András Kotschy, Tetrahedron 2008, 64, 8992-8996. DOI10.1016/j.tet.2008.05.100 |

An efficient one-pot protocol was developed for the construction of the benzofuran system from aryl halides and protected iodophenols using carbinol-based acetylene sources. The sequence includes alternating palladium-catalyzed Sonogashira couplings and deprotection steps concluded by a ring closure. The developed one-pot procedure was compared with the stepwise approach and its efficiency was also demonstrated by the total synthesis of vignafuran, a benzofuran natural product.