Palladium-Catalyzed ortho-Selective C[BOND]H Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles


  • We gratefully acknowledge The Scripps Research Institute and the US NSF (CHE-1011898) for financial support. We thank the US EPA (STAR predoctoral fellowship for P.S.T.-B., Assistance Agreement no. FP917296-01-0), the Swiss National Science Foundation (postdoctoral fellowship for G.V.), and MINCINN (FPI fellowship for A.H.).


We disclose a protocol for the palladium-catalyzed ortho-selective C[BOND]H deuteration of arenes. Phenylacetic acids and benzoic acids are suitable substrates for this reaction. This reaction offers a catalytic route to ortho-deuterated phenylacetic acids and benzoic acids and demonstrates the sharp difference in reactivity of palladacycle intermediates held together by weak and strong coordination.