I2-mediated regioselective C-3 azidation of indoles

Abstract

An unprecedented synthesis of novel 3-azido indoles has been developed using I₂ and NaN₃ 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 I₂.