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Synfacts 2009(5): 0492-0492  
DOI: 10.1055/s-0029-1216607
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Benzo-[b]naphtho-[2,1-d]furans via a Domino Process

Contributor(s): Victor Snieckus, Josefine Karlsson
X.-C. Huang, F. Wang, Y. Liang*, J.-H. Li*
Hunan Normal University, Changsha and Wenzhou University, P. R. of China
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Publikationsverlauf

Publikationsdatum:
22. April 2009 (online)

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Significance

Described here is a general halopalladation/decarboxylation/carbon-carbon forming domino protocol for the synthesis of 5-halo-6-substituted benzo[b]naphtho[2,1-d]furans. Numerous 2-[2-(ethynyl)phenyl]-benzofuran-3-carboxylates undergo an intramolecular decar-bonylative coupling to capture the σ-vinylpalladium intermediate in situ in the presence of PdCl2 and CuX2 (X = Cl, Br).