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<p>Multisubstituted azaarenes and conjugated polyazaarenes are important heterocycles in chemistry and materials science. Here we report the discovery of a carbon–carbon bond cleavage and alkyl transfer approach for the synthesis of azaarenes or conjugated polyazaarenes, which is promoted by potassium <i>tert</i>-butoxide. Neither precious-metal catalysts nor directing groups are required. This strategy is enabled by an alkyl transfer, releasing aryl methanes, such as toluene, as the only by-product. This general and versatile method enables the divergent synthesis of a variety of highly functionalized azaarenes and polyazaarenes. In addition, several azaarenes were found to have visible-light photocatalytic reactivities.</p><p></p>

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Base-promoted azaarene and polyazaarene synthesis through C–C bond cleavage and alkyl transfer

  • 期刊论文

  • 发表日期：

    2025年7月17日

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  • Yong-Ze Chen,
  • Xiang-Huan Shan,
  • Bo Yang,
  • Lin Tie,
  • Yu Liu,
  • Jia-Le Fu,
  • Jian-Ping Qu,
  • Yan-Biao Kang

摘要

Multisubstituted azaarenes and conjugated polyazaarenes are important heterocycles in chemistry and materials science. Here we report the discovery of a carbon–carbon bond cleavage and alkyl transfer approach for the synthesis of azaarenes or conjugated polyazaarenes, which is promoted by potassium tert-butoxide. Neither precious-metal catalysts nor directing groups are required. This strategy is enabled by an alkyl transfer, releasing aryl methanes, such as toluene, as the only by-product. This general and versatile method enables the divergent synthesis of a variety of highly functionalized azaarenes and polyazaarenes. In addition, several azaarenes were found to have visible-light photocatalytic reactivities.