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Dearomative Ring Expansion of Polycyclic Arenes.

Paolo PiacentiniTanner W BinghamDavid Sarlah
Published in: Angewandte Chemie (International ed. in English) (2022)
Benzocycloheptenes constitute a common structural motif embedded in many natural products and biologically active compounds. Herein, we report their concise preparation from non-activated polycyclic arenes using a two-step sequence involving dearomative [4+2]-cycloaddition with arenophile in combination with palladium-catalyzed cyclopropanation, followed by cycloreversion-initiated ring expansion. The described strategy provides a working alternative to the Buchner reaction, which is limited to monocyclic arenes. Overall, this methylene-insertion molecular editing approach enables rapid and direct conversion of simple (hetero)arenes into a range of substituted (aza)benzocycloheptatrienes, which can undergo a myriad of downstream functionalizations.
Keyphrases
  • crispr cas
  • molecular docking
  • high resolution