Installation of O‐Heterocycles to N‐Heteroarenes via an Et<sub>3</sub>B/O<sub>2</sub>‐Mediated Radical Reaction of α‐Alkoxy and α‐Alkoxyacyl Tellurides

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  • Daiki Kuwana
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Benjamin Ovadia
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Daigo Kamimura
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Masanori Nagatomo
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
  • Masayuki Inoue
    Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan

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<jats:title>Abstract</jats:title><jats:p>We report a radical‐based method that links highly oxygenated O‐heterocycles and N‐heteroarenes. Treatment of α‐alkoxy or α‐alkoxyacyl tellurides with Et<jats:sub>3</jats:sub>B under air at room temperature generated α‐alkoxy carbon radicals, which were then added to protonated N‐heteroarenes. Regeneration of aromaticity proceeded in situ without an additional oxidant, leading to O‐heterocycle‐functionalized N‐heteroarenes. The present method enables the formation of hindered C(sp<jats:sup>3</jats:sup>)−C(sp<jats:sup>2</jats:sup>) bonds between five O‐heterocycles and five N‐heteroarenes under mild conditions.</jats:p>

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