Here we report an alternative approach to the regioselective synthesis of C2-borylated indoles. A Larock-type annulation allows regioselective synthesis of functionalized 2-borylated indoles under mild conditions (Scheme 1c). The process avoids the need for protecting groups on the indole nitrogen and avoids the restrictions imposed by using commercial indole scaffolds. The utility of this approach is demonstrated in the synthesis of drug scaffolds and alkaloid natural products.