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Aerobic Direct C(sp2)‑H Hydroxylation of 2‑Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation

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journal contribution
posted on 09.08.2016, 00:00 authored by Prasenjit Das, Debajyoti Saha, Dibyajyoti Saha, Joyram Guin
Herein we present a Pd-catalyzed direct C–H hydroxylation of 2-arylpyridines using molecular oxygen (O2) as the sole oxidant. The key aspects of the method include: (a) the activation of molecular oxygen with a nontoxic and inexpensive aldehyde; (b) an efficient association of the in situ-generated acyl peroxo radical with palladium catalysis; and (c) convenient operating conditions. On the basis of the results obtained in a series of control experiments, a PdII/PdIV catalytic cycle is implicated for the transformations. Furthermore, the method offers an easy access to a broad range of substituted 2-(pyridin-2-yl)­phenols in good isolated yields.

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