Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction

Anne-Doriane Manick (1) , Bruno Salgues (2) , Jean-Luc Parrain (1) , Elena Zaborova (2) , Frédéric Fages (2) , Muriel Amatore (1) , Laurent Commeiras (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille

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-alkoxy-indenones as surrogates of the highly reactive benzocyclopentynone 2 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.

Mots clés: Cycloaddition; fluorenone; alkyne surrogate

Domaines: Chimie organique

Anne-Doriane Manick, Bruno Salgues, Jean-Luc Parrain, Elena Zaborova, Frédéric Fages, et al.. Access to Fluorenones Using Benzocyclopentynone Surrogate as Partner for the [2 + 2 + 2] Cycloaddition Reaction. Illustration. France. 2020. ⟨hal-02873541⟩