This report discloses an electrochemical oxidative CÀ H/NÀ H cross coupling method for the synthesis of C-2/C-3 azolated halo-indoles/thiophenes under metal catalyst-free and external chemical oxidant free condition. Hydrogen gas was the only byproduct of this CÀ H/NÀ H cross-coupling reaction. The synthetic utility of this electrochemical approach is highlighted by its easy scalabity and compatibility with highly functional indoles and azoles. The retention of halogen on the heterocycles could serve as a useful functional group for future late-stage modifications.