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<p>We report a NaHMDS-promoted strategy for the efficient and highly selective synthesis of aryl diboronates from carbonyl compounds through controlled activation of diboron reagents. This transformation proceeds under catalyst- and additive-free conditions and offers notable advantages, including environmental sustainability, avoidance of halogenated waste, and broad functional-group compatibility. The protocol enables late-stage diborylation of biologically relevant molecules and provides a versatile platform for accessing structurally diverse naphthalene derivatives directly from carbonyl precursors. Combined experimental and computational studies indicate that the reaction proceeds via sequential alkenyl C–O bond borylation, allylic C–H bond borylation, and a desaturation process. Remarkably, the diboron reagent exhibits an unprecedented oxidative role rather than its conventional reductive behavior, ing a hydride from an anionic alkenyl boronate intermediate to promote desaturation. These findings reveal a previously unrecognized reactivity mode of base/diboron reagent systems and open new avenues for reaction design based on their oxidative potential.</p>

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Controlled desaturative diborylation of carbonyls

  • 期刊论文

  • 发表日期：

    2026年4月14日

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  • Chaoqun Shi,
  • Cheng Ma,
  • Xinni An,
  • Minghui Sun,
  • Shasha Geng,
  • Yun He,
  • Yi Yang,
  • Shaofei Ni,
  • Zhang Feng

摘要

We report a NaHMDS-promoted strategy for the efficient and highly selective synthesis of aryl diboronates from carbonyl compounds through controlled activation of diboron reagents. This transformation proceeds under catalyst- and additive-free conditions and offers notable advantages, including environmental sustainability, avoidance of halogenated waste, and broad functional-group compatibility. The protocol enables late-stage diborylation of biologically relevant molecules and provides a versatile platform for accessing structurally diverse naphthalene derivatives directly from carbonyl precursors. Combined experimental and computational studies indicate that the reaction proceeds via sequential alkenyl C–O bond borylation, allylic C–H bond borylation, and a desaturation process. Remarkably, the diboron reagent exhibits an unprecedented oxidative role rather than its conventional reductive behavior, ing a hydride from an anionic alkenyl boronate intermediate to promote desaturation. These findings reveal a previously unrecognized reactivity mode of base/diboron reagent systems and open new avenues for reaction design based on their oxidative potential.