4.8 Article

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

Journal

ORGANIC LETTERS
Volume 22, Issue 5, Pages 1894-1898

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00235

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Funding

  1. Excellence Initiative of Aix-Marseille University A*MIDEX
  2. French Investissement d'Avenir program
  3. CNRS
  4. MRES
  5. AMU

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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 2 pi 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.

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