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<p>Functional groups are central to organic chemistry. Their composition, spatial orientation and specific location can influence a molecule’s behaviour. The direct, precise ‘editing’ of the position of a given functional group without altering other parts of the molecule represents a strategy that is complementary to traditional retrosynthetic logic and valuable for late-stage molecular diversification. However, with the exception of alkene isomerization, general methods for such positional editing remain scarce, often relying on specialized substrates or equilibrium processes. Here we report a catalytic 1,2-transposition of a pinacol boryl group that occurs across a wide range of substrates. By harnessing the versatility of organoboron compounds as synthetic intermediates, our method enables a three-step platform for formal positional editing of a diverse set of functional groups, allowing access to corresponding positional isomers. Key to our design is the identification of suitable hydrogen-atom transfer catalysts and conditions, which govern the reaction efficiencies, directions and selectivities.</p><p></p>

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Positional editing of diverse functional groups through radical 1,2-boron shifts

  • 期刊论文

  • 发表日期：

    2026年3月12日

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  • Wenwen Zhang,
  • Shuxin Mao,
  • Mengqi Peng,
  • Yumeng Xi

摘要

Functional groups are central to organic chemistry. Their composition, spatial orientation and specific location can influence a molecule’s behaviour. The direct, precise ‘editing’ of the position of a given functional group without altering other parts of the molecule represents a strategy that is complementary to traditional retrosynthetic logic and valuable for late-stage molecular diversification. However, with the exception of alkene isomerization, general methods for such positional editing remain scarce, often relying on specialized substrates or equilibrium processes. Here we report a catalytic 1,2-transposition of a pinacol boryl group that occurs across a wide range of substrates. By harnessing the versatility of organoboron compounds as synthetic intermediates, our method enables a three-step platform for formal positional editing of a diverse set of functional groups, allowing access to corresponding positional isomers. Key to our design is the identification of suitable hydrogen-atom transfer catalysts and conditions, which govern the reaction efficiencies, directions and selectivities.