Intramolecular Benzyne–Phenolate [4+2] Cycloadditions

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  • Hiroshi Takikawa
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Arata Nishii
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Hiromu Takiguchi
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Hirotoshi Yagishita
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Masato Tanaka
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Keiichi Hirano
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Masanobu Uchiyama
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Ken Ohmori
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan
  • Keisuke Suzuki
    Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551 Japan

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<jats:title>Abstract</jats:title><jats:p>An intramolecular benzyne–phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen‐sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph<jats:sub>3</jats:sub>MgLi or <jats:italic>n</jats:italic>BuLi for halogen–metal exchange to form various benzobarrelenes.</jats:p>

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