Given the importance of deuterated indoles, a significant amount of work has gone into developing strategies for their deuteration (Scheme 1A): Heterogeneous catalysis generally affords global deuteration of all free positions (2); more recently a metal-free approach has also been reported. Deuteration on the pyrrole moiety (C2 and C3, 3) has been achieved with ruthenium nanoparticles, rhodium, or under homogeneous Ag2CO3 catalysis. Under acid/base-mediated conditions, selective deuterium-incorporation at C3 is controlled by the molecule's intrinsic reactivity (4). Similar reactivity has been achieved using organocatalysts, 21 Ru3(CO)12, or AgOTf. Selective deuteration at C2 can currently only be achieved using directed approaches (5): ortho-lithiation or transition-metal catalyzed methods requiring a directing group on the indole nitrogen. Directing group removal is not always straightforward, andcruciallycan cause isotopic dilution if strong acidic or basic conditions are required. Therefore, a directing group free method for C2-deuteration would be highly beneficial. Herein, we report a directing group free, palladium-catalyzed C2-selective deuteration, using an air-stable, readily available palladium catalyst and a userfriendly source of deuterium (Fig. ).