Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
Tania Medina-Gil, Anna Sadurní, L. Anders Hammarback, Antonio M. Echavarren
Abstract
High Resolution Image Download MS PowerPoint Slide Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of o -allylphenols with acetylene gas that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the natural product lapachol.
Topics & Concepts
RegioselectivityAlkyneAlkeneAcetyleneChemistryCatalysisCarbeneIntermolecular forceNucleophileOrganic chemistryCombinatorial chemistryPhotochemistryMoleculeCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods