Azaheterocycles are prolific in agrochemicals, pharmaceuticals, and natural products. Among the variety of classes, indole remains a template of enduring prominence. The academic and industrial utility of this scaffold has inspired the development of numerous methodologies for its construction and functionalization. Selective functionalization of the indole scaffold has been integral to the development of bioactive compounds (e.g., Scheme 1a) and strategies that allow selective and/or late-stage modification remain a target for methodological development. Based on their wide scope of potential applications and familiarity of use, methods to install boron functional groups have been a particular target for development. These methods include classical strategies based on stoichiometric metalation and reaction with, for example, B(OMe)3, and extend to contemporary approaches using C-H activation and direct borylation with borenium cations (Scheme 1b). 6 Scheme 1. Accessing borylated indoles. Cat. = catalyst, MIDA = N-methyliminodiacetoxy, Pin = pinacolato, TM = transition metal.