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Catalytic α‑Selective Deuteration of Styrene Derivatives

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journal contribution
posted on 09.01.2019 by Thomas R. Puleo, Alivia J. Strong, Jeffrey S. Bandar
We 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.