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ELECTROCHEMICAL SYNTHESIS

Ready and label

Electrochemical deuteration of unactivated alkyl halides provides a general, efficient and sustainable method to prepare deuterium-labelled alkanes.

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Fig. 1: Deuteration of organic halides for synthesis of deuterium-labelled compounds.

References

  1. Urey, H. C., Brickwedde, F. G. & Murphy, G. M. A hydrogen isotope of mass 2 and its concentration. Phys. Rev. 40, 1–15 (1932).

    Article  CAS  Google Scholar 

  2. Wiberg, K. B. The deuterium isotope effect. Chem. Rev. 55, 913–743 (1955).

    Article  Google Scholar 

  3. Cockrell, J. R. & Murray, R. W. Deuterium labeling by electrochemical reactions. J. Electrochem. Soc. 119, 849–851 (1972).

    Article  CAS  Google Scholar 

  4. Xia, A., Xie, X., Hu, X., Xu, W. & Liu, Y. Dehalogenative deuteration of unactivated alkyl halides using D2O as the deuterium source. J. Org. Chem. 84, 13841–13857 (2019).

    Article  CAS  Google Scholar 

  5. Soulard, V., Villa, G., Vollmar, D. P. & Renaud, P. Radical deuteration with D2O: catalysis and mechanistic insights. J. Am. Chem. Soc. 140, 155–158 (2018).

    Article  CAS  Google Scholar 

  6. Li, Y. et al. Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides. Nat. Commun. 12, 2894 (2021).

    Article  CAS  Google Scholar 

  7. Li, P. et al. Facile and general electrochemical deuteration of unactivated alkyl halides. Nat. Commun. 13, 3774 (2022).

    Article  CAS  Google Scholar 

  8. Dong, X. et al. Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations. Science 371, 507–514 (2021).

    Article  CAS  Google Scholar 

  9. Ma, C. et al. Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts. Sci. Bull. 66, 2412–2429 (2021).

    Article  CAS  Google Scholar 

  10. Huang, H., Steiniger, K. A. & Lambert, T. H. Electrophotocatalysis: combining light and electricity to catalyze reactions. J. Am. Chem. Soc. 144, 12567–12583 (2022).

    Article  CAS  Google Scholar 

Download references

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Correspondence to Da-Gang Yu.

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Ran, CK., Yu, DG. Ready and label. Nat Rev Chem 6, 679–680 (2022). https://doi.org/10.1038/s41570-022-00428-z

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