Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction
Anne‐Doriane Manick, Bruno Salgues, Jean‐Luc Parrain, Elena Zaborova, Fréderic Fagès, Muriel Amatore, Laurent Comméiras
Abstract
A convenient and versatile procedure for the straightforward synthesis of substituted fluorenones as valuable scaffolds is described under rhodium catalysis. The present [2 + 2 + 2] cycloaddition reaction of diynes with 3-acetoxy or-3-alkoxyindenones as surrogates of the highly reactive benzocyclopentynone 2π partner allows the preparation of various fluorenone-type derivatives in good yields and provides an additional and tunable process for the generation of more challenging molecules with application in pharmaceutical, polymer, and material sciences.
Topics & Concepts
CycloadditionChemistryFluorenoneCombinatorial chemistryRhodiumCatalysisMoleculeOrganic chemistryPolymerFluoreneCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions