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

Article abstract of DOI:10.1016/j.tet.2011.04.092

The heterobimetallic complex [Ir(COD)(SnCl₃)Cl(μ-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.