Stereoselective transformation of alkynes to (Z)-β-deuterated vinyl sulfones using phosphoryl radical as a halogen atom transfer agent.

Herein, we report a one-pot, two-step, phosphoryl radical-mediated reductive deutero-dehalogenation of in situ-generated halo vinyl sulfones, enabling straightforward access to various β-deuterated vinyl sulfones using relatively inexpensive D2O as the deuterium source. This methodology directly transforms alkynes into thermodynamically less stable Z-Michael acceptors with substantial deuterium incorporation under environmentally benign conditions. Additionally, it tolerates a variety of functional groups, and halogen atom transfer from the vinylic position demonstrates excellent chemoselectivity.