Acid-Catalyzed Cascade Reaction of 2-Alkylfurans with α,β-Unsaturated Ketones: A Shortcut to 2,3,5-Trisubstituted Furans

J Org Chem. 2021 Dec 3;86(23):17362-17370. doi: 10.1021/acs.joc.1c01692. Epub 2021 Nov 16.

Abstract

The convergent one-pot method toward trisubstituted furans has been developed. The key transformation behind the synthetic protocol comprises the cascade acid-catalyzed conjugated addition of furans to commercially available or easily accessible α,β-unsaturated ketones followed by the rearrangement of the intermediate Michael adducts into isomeric furans. The prospect of utilizing the target products as building blocks for the preparation of potential functional molecules for organic electronics has been demonstrated.