Synthesis of Benzo[<i>b</i>]furans by Intramolecular C–O Bond Formation Using Iron and Copper Catalysis
Martyn C. Henry, Andrew Sutherland
Abstract
One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.
Topics & Concepts
ChemistryIntramolecular forceRegioselectivityCatalysisFuranRing (chemistry)HalogenationArylCopperMedicinal chemistryTransition metalStereochemistryCombinatorial chemistryOrganic chemistryAlkylCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms