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Remarkably High Reactivity of Pd(OAc)2/Pyridine Catalysts: Nondirected C[BOND]H Oxygenation of Arenes

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  • We thank the NSF for support of this work through the Center for Enabling New Technologies through Catalysis (CENTC), and Professors Karen Goldberg, Bill Jones, Mike Heinekey, Elon Ison, and Jim Mayer for valuable discussions. M.H.E. thanks the Deutsche Forschungsgemeinschaft for a postdoctoral fellowship. A.K.C. thanks the Rackham Graduate School for a predoctoral fellowship. Y.J.X. thanks CENTC for a summer undergraduate fellowship. We also thank J. Brannon Gary and Dr. Dipannita Kalyani for editorial assistance.

Abstract

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Less is more: The rational optimization and general applicability of the catalytic system Pd(OAc)2/pyridine is described (see scheme). The catalyst shows excellent reactivity in the C[BOND]H oxygenation of simple aromatic substrates. The Pd/pyridine ratio is critical as the use of one equivalent of pyridine per Pd center leads to dramatic enhancements in both reactivity and site selectivity in comparison to Pd(OAc)2 alone.

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