Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: synthesis of fully decorated furans and pyrroles

The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the direct substitution of hydroxyl groups in benzylic and propargylic alcohols by 1,3-dicarbonyl moiety. In 4-hydroxycoumarin, benzylation and propargylation occurs at the 3-position. Selective propargylation or allenylation takes place depending on the nature of propargylic alcohol. By applying the methodology, multi-substituted furans and pyrroles have been synthesized in good yields. (C) 2011 Elsevier Ltd. All rights reserved.