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<p>Deuterated N-heteroarenes are important for applications in pharmaceuticals and materials science. However, their synthesis from hydrogen isotope exchange reactions requires expensive isotopic sources (D<sub>2</sub>, C<sub>2</sub>H<sub>5</sub>OD, C<sub>6</sub>D<sub>6</sub>), metal complexes or hazardous conditions (≥120 °C and 20 bar H<sub>2</sub>). Here we demonstrate a photocatalytic synthetic route to deuterated N-heteroarenes in D<sub>2</sub>O at room temperature under 410 nm irradiation and inert atmosphere over an atomically dispersed palladium photocatalyst (Pd<sub>1</sub>/TiO<sub>2</sub>). This method demonstrates hydrogen isotope exchange of 62 N-heteroarenes with high deuterium incorporation (0.55–4.77 deuterium per molecule). By recycling used photocatalysts and D<sub>2</sub>O, up to 1.157 kg (11.93 mol) deuterated 2-aminopyrimidine-4,6-<i>d</i><sub>2</sub> (90–99% deuterium incorporation) is produced and isolated using only 4.5 litres D<sub>2</sub>O (249 mol, 19.7 equiv.). Mechanism investigations reveal that partially reduced single-atom Pd species, in situ formed via photo-generated electrons, could be the main active sites for photocatalytic hydrogen isotope exchange.</p><p></p>

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Scalable light-driven deuteration of N-heteroarenes over atomically dispersed palladium

  • 期刊论文

  • 发表日期：

    2026年1月26日

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  • Jie Xu,
  • Rui Cao,
  • Shao-Zhen Yang,
  • Yi-Ming Guo,
  • Tong Xia,
  • Da Zhao,
  • Tingrui Pan,
  • K. M. Liew,
  • Flemming Besenbacher,
  • Yi-Tao Dai

摘要

Deuterated N-heteroarenes are important for applications in pharmaceuticals and materials science. However, their synthesis from hydrogen isotope exchange reactions requires expensive isotopic sources (D2, C2H5OD, C6D6), metal complexes or hazardous conditions (≥120 °C and 20 bar H2). Here we demonstrate a photocatalytic synthetic route to deuterated N-heteroarenes in D2O at room temperature under 410 nm irradiation and inert atmosphere over an atomically dispersed palladium photocatalyst (Pd1/TiO2). This method demonstrates hydrogen isotope exchange of 62 N-heteroarenes with high deuterium incorporation (0.55–4.77 deuterium per molecule). By recycling used photocatalysts and D2O, up to 1.157 kg (11.93 mol) deuterated 2-aminopyrimidine-4,6-d2 (90–99% deuterium incorporation) is produced and isolated using only 4.5 litres D2O (249 mol, 19.7 equiv.). Mechanism investigations reveal that partially reduced single-atom Pd species, in situ formed via photo-generated electrons, could be the main active sites for photocatalytic hydrogen isotope exchange.