Efficient reductive deuteration of thioamides using SmI? with D?O

Deuterium-labeled compounds have found numerous applications in various areas of science,[1] including medicinal chemistry [2] due to their enhanced metabolic stability. Since 2004, at ATLANCHIM PHARMA , having already prepared more than 350 labeled compounds for our customers, we are attentive to new and efficient methodologies to introduce isotopes into organic products, to always offer the best. As an alternative to reduction of amides with LiAlD? to prepare α,α?dideuterio amines, an efficient and chemoselective procedure for the single-electron-transfer reductive deuteration of thioamides using SmI? and D?O as deuterium source has recently been reported, as exemplified in the Scheme below. [3]

[1] H.-H. Zhang et al., Org. Lett. 2021, 23, 1554-1560 and cited literature.

[2] J. Chang et al., J. Med. Chem. 2021, 64, 925-937 and cited literature.

[3] Li, K. Wang, W. Zhao, X. Li, Y. Fu, H. Do, J. An, Z. Hu, Org. Lett. 2024, 26, 9120-9125.