DFT Studies on the Mechanism of the Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylene with Alkenes

Hideaki Takano, Natsuhiko Sugimura, Stephen Kyalo Kanyiva, Takanori Shibata

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3 Citations (Scopus)


Recently, we reported an Ir-catalyzed formal [4 + 1] cycloaddition of biphenylenes with alkenes, which gave 9,9-disubstituted fluorenes in moderate to excellent yields. We proposed a reaction mechanism that involved the intermolecular insertion of alkenes, β-elimination, and intramolecular insertion based on the results of experimental mechanistic studies. Herein, we further support the proposed mechanism by density functional theory calculations and explain why [4 + 1] cycloaddition proceeds rather than conventional [4 + 2] cycloaddition.

Original languageEnglish
Pages (from-to)5228-5234
Number of pages7
JournalACS Omega
Issue number8
Publication statusPublished - 2017 Jan 1


ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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