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<p>Migratory functionalization of C–H bonds through metal migration from carbon to carbon under transition metal catalysis is a process of significant academic and industrial interest. Herein, a palladium-catalyzed migratory cyclization of <i>α</i>-bromoalkene derivatives ArXCBr=CH<sub>2</sub>, in which X denotes a phosphorus (P(O)R), silicon (SiR<sub>2</sub>), sulfur (SO<sub>2</sub>), carbon (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the cyclization reaction proceeds through an unexpected cascade, with <i>trans</i>-1,2-palladium migration between sp<sup>2</sup> carbons being a key step of catalytic cycle. To the best of our knowledge, this type of metal migration has not been reported previously.</p>

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Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年4月9日

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  • Wen-Cong Li,
  • Lin Zhang,
  • Shiming Bai,
  • Jia-Hao Zhao,
  • Guang-Rui Liu,
  • Yu Lan,
  • Shufeng Chen,
  • Jialin Ming

摘要

Migratory functionalization of C–H bonds through metal migration from carbon to carbon under transition metal catalysis is a process of significant academic and industrial interest. Herein, a palladium-catalyzed migratory cyclization of α-bromoalkene derivatives ArXCBr=CH2, in which X denotes a phosphorus (P(O)R), silicon (SiR2), sulfur (SO2), carbon (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the cyclization reaction proceeds through an unexpected cascade, with trans-1,2-palladium migration between sp2 carbons being a key step of catalytic cycle. To the best of our knowledge, this type of metal migration has not been reported previously.