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Updated: Jan 20, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
DFT Studies on the Mechanism of the Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylene with Alkenes
Hideaki Takano1, Natsuhiko Sugimura1, Kyalo Stephen Kanyiva1
1Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Materials Characterization Central Laboratory, and International Center for Science and Engineering Program (ICSEP), Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Abstract:
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.
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