ja8b12874_si_001.pdf (4.89 MB)
Catalytic α‑Selective Deuteration of Styrene Derivatives
journal contribution
posted on 2019-01-09, 00:00 authored by Thomas
R. Puleo, Alivia J. Strong, Jeffrey S. BandarWe
report an operationally simple protocol for the catalytic α-deuteration
of styrenes. This process proceeds via the base-catalyzed reversible
addition of methanol to styrenes in DMSO-d6 solvent. The concentration of methanol is shown to be critical for
high yields and selectivities over multiple competing side reactions.
The synthetic utility of α-deuterated styrenes for accessing
deuterium-labeled chiral benzylic stereocenters is demonstrated.