I2-mediated regioselective C-3 azidation of indolesElectronic supplementary information (ESI) available. See DOI: 10.1039/c6ob00295a

An unprecedented synthesis of novel 3-azido indoles has been developed using I 2 and NaN 3 in high yields and excellent regioselectivity. The reaction proceeds under metal-free conditions at room temperature. Essentially, an umpolung in reactivity at the C-3 position of indole has been achieved by the activation of indoles with I 2 . An unprecedented synthesis of novel 3-azido indoles has been developed using I 2 and NaN 3 in high yields and excellent regioselectivity.