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<p>Deuterium-labelled compounds play a crucial role in drug discovery as both diagnostic tools and deuterated pharmaceuticals. While hydrogen isotope exchange is well established for activated substrates, the catalytic deuteration of unactivated amides and esters remains underdeveloped, particularly under mild conditions suitable for sensitive pharmaceuticals and polymers. This limitation hampers the late-stage modification of pharmaceutical molecules and functional materials. Here we report a catalytic hydrogen isotope exchange method using cooperative catalysts—a silicon Lewis acid and a tertiary amine base—functioning as a frustrated Lewis pair. This approach enables highly selective deuteration under mild conditions. Our method achieves high deuterium incorporation in various functionalized pharmaceuticals and polyesters, including those typically unstable under basic conditions, demonstrating its broad applicability.</p><p></p>

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Silicon frustrated Lewis pairs catalyse α-deuteration of amides and esters

  • 期刊论文

  • 发表日期：

    2025年10月24日

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  • Y. Koga,
  • I. Fukumoto,
  • K. Masui,
  • T. Tanaka,
  • Y. Naganawa,
  • M. Hayashi,
  • T. Ohshima,
  • R. Yazaki

摘要

Deuterium-labelled compounds play a crucial role in drug discovery as both diagnostic tools and deuterated pharmaceuticals. While hydrogen isotope exchange is well established for activated substrates, the catalytic deuteration of unactivated amides and esters remains underdeveloped, particularly under mild conditions suitable for sensitive pharmaceuticals and polymers. This limitation hampers the late-stage modification of pharmaceutical molecules and functional materials. Here we report a catalytic hydrogen isotope exchange method using cooperative catalysts—a silicon Lewis acid and a tertiary amine base—functioning as a frustrated Lewis pair. This approach enables highly selective deuteration under mild conditions. Our method achieves high deuterium incorporation in various functionalized pharmaceuticals and polyesters, including those typically unstable under basic conditions, demonstrating its broad applicability.