Study of the Pauson–Khand reaction in flow over alkynylphenyl vinyl ethers: towards the synthesis of tricyclic multisubstituted benzofurans

Abstract

The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson–Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the substrate decomposition allowing the formation of the PK adduct. Substrates substituted at the internal position of the double bond and with internal triple bonds give better yields. The resulting products are cyclopentabenzofuranones present in diverse natural products and drugs that can be further functionalised.