Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes
- 14 January 2011
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (4), 1134-1139
- https://doi.org/10.1021/jo1023987
Abstract
2,5-Disubstituted 3-iodofurans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of (Z)-β-bromoenol acetates and terminal alkynes, followed by iodocyclization. The useful intermediates conjugated enyne acetates are obtained in high yields in the transformation. Aryl- and alkyl-substituted alkynes undergo iodocyclization in good yields. The resulting iodine-containing furans can be readily elaborated to 2,3,5-trisubstituted furans.Keywords
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