Electrochemical Oxidative C3 Acyloxylation of Imidazo[1,2-a]pyridines with Hydrogen Evolution.

The C3-functionalized imidazo[1,2-a]pyridines are versatile nitrogen-fused heterocycles; however, the methods for the C3 acyloxylation of imidazo[1,2-a]pyridines have never been reported. Herein we demonstrate the electrochemical oxidative C3 acyloxylation of imidazo[1,2-a]pyridines for the first time. Notably, by using electricity, the electrochemical oxidative C3 acyloxylation of imidazo[1,2-a]pyridines was carried out under mild conditions. Moreover, in addition to aromatic carboxylic acids, alkyl carboxylic acids were also competent substrates.

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions.

An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.