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-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.

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. Organic Letters, 2020, 22 (5), pp.1894-1898. ⟨10.1021/acs.orglett.0c00235⟩. ⟨hal-02873529⟩