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Controllable deuteration of halogenated compounds by photocatalytic D2O splitting.

Cuibo LiuZhongxin ChenChenliang SuXiaoxu ZhaoQiang GaoGuo-Hong NingHai ZhuWei TangKai LengWei FuBingbing TianXinwen PengJing LiQing-Hua XuWu ZhouKian Ping Loh
Published in: Nature communications (2018)
Deuterium labeling is of great value in organic synthesis and the pharmaceutical industry. However, the state-of-the-art C-H/C-D exchange using noble metal catalysts or strong bases/acids suffers from poor functional group tolerances, poor selectivity and lack of scope for generating molecular complexity. Herein, we demonstrate the deuteration of halides using heavy water as the deuteration reagent and porous CdSe nanosheets as the catalyst. The deuteration mechanism involves the generation of highly active carbon and deuterium radicals via photoinduced electron transfer from CdSe to the substrates, followed by tandem radicals coupling process, which is mechanistically distinct from the traditional methods involving deuterium cations or anions. Our deuteration strategy shows better selectivity and functional group tolerances than current C-H/C-D exchange methods. Extending the synthetic scope, deuterated boronic acids, halides, alkynes, and aldehydes can be used as synthons in Suzuki coupling, Click reaction, C-H bond insertion reaction etc. for the synthesis of complex deuterated molecules.
Keyphrases
  • electron transfer
  • highly efficient
  • quantum dots
  • ionic liquid
  • metal organic framework
  • reduced graphene oxide
  • room temperature
  • visible light
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  • single molecule
  • structural basis