Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction.
Anne-Doriane ManickBruno SalguesJean-Luc ParrainElena ZaborovaFrédéric FagesMuriel AmatoreLaurent CommeirasPublished in: Organic letters (2020)
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.