Electrochemical deuteration of unactivated alkyl halides provides a general, efficient and sustainable method to prepare deuterium-labelled alkanes.
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Urey, H. C., Brickwedde, F. G. & Murphy, G. M. A hydrogen isotope of mass 2 and its concentration. Phys. Rev. 40, 1–15 (1932).
Wiberg, K. B. The deuterium isotope effect. Chem. Rev. 55, 913–743 (1955).
Cockrell, J. R. & Murray, R. W. Deuterium labeling by electrochemical reactions. J. Electrochem. Soc. 119, 849–851 (1972).
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).
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).
Li, Y. et al. Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides. Nat. Commun. 12, 2894 (2021).
Li, P. et al. Facile and general electrochemical deuteration of unactivated alkyl halides. Nat. Commun. 13, 3774 (2022).
Dong, X. et al. Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations. Science 371, 507–514 (2021).
Ma, C. et al. Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts. Sci. Bull. 66, 2412–2429 (2021).
Huang, H., Steiniger, K. A. & Lambert, T. H. Electrophotocatalysis: combining light and electricity to catalyze reactions. J. Am. Chem. Soc. 144, 12567–12583 (2022).
The authors declare no competing interests.
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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