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<p>Herein, we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid (HCl) and <i>N</i>-chlorosuccinimide (NCS), which is significantly different from conventional migration modes under basic conditions. In this protocol, HCl, as the first electrophile, activates the C≡C bond, triggering the first 1,2-aryl migration. Subsequently, NCS promotes a secondary metallate shift, enabling the construction of polysubstituted alkenes. Notably, this process can work well under mild conditions, exhibits high efficiency, and provides valuable products. This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions, it can proceed smoothly under acidic conditions as well, which greatly expands the scope of this well-known olefination reaction.</p>

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Two distinct electrophiles enabled sequential dual migrations of alkynyl tetracoordinate borons

  • 期刊论文

  • 发表日期：

    2025年6月4日

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  • Hejun An,
  • Wei Zhu,
  • Mengwei Tan,
  • Meihui Cai,
  • Yi Huang,
  • Xingxing Ma,
  • Qiuling Song

摘要

Herein, we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid (HCl) and N-chlorosuccinimide (NCS), which is significantly different from conventional migration modes under basic conditions. In this protocol, HCl, as the first electrophile, activates the C≡C bond, triggering the first 1,2-aryl migration. Subsequently, NCS promotes a secondary metallate shift, enabling the construction of polysubstituted alkenes. Notably, this process can work well under mild conditions, exhibits high efficiency, and provides valuable products. This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions, it can proceed smoothly under acidic conditions as well, which greatly expands the scope of this well-known olefination reaction.