A review. The indole framework is one of the ubiquitous heterocycles in natural products and pharmaceuticals. Thus, various methods have been developed to afford functionalized indoles. Recently, direct functionalization of indoles at the C7 position has been emerged. Introduction of directing groups such as hydrosilyl, phosphinoyl, and pivaloyl group at the N1 position represented by formula I (X, Y, X = directing group) enables site-selective functionalization via coordination to metal catalysts depicted by formula II (M = metal such as palladium indium, rhodium, or indium; X,Y,Z = directing group). In these cases, bulkiness of the directing group is found to be crucial for high reactivity and C7-selectivity. Examples include (1) pinacolatoborylation of indole by in situ silylation with diethylsilane in the presence of a Ru complex and borylation with bis(pinacolato)diboron in the presence of a iridium complex to give indole-7-boronic acid pinacol ester (III), (2) arylation (cross-coupling) of 1-(dibutylphosphoryl)-1H-indole with arylboronic acids in the presence of palladium acetate to give 7-aryl-1-(dibutylphosphoryl)-1H-indoles (IV), (3) alkenylation of 1-pivaloyl-1H-indole by Me acrylate in the presence of a rhodium complex and copper(II) acetate to give Me 3-(1-pivaloyl-1H-indol-7-yl)acrylate (V), and (4) sulfonylamination of 1-pivaloyl-1H-indole by RSO2N3 in the presence of a iridium complex and AgNTf2 to give 1-pivaloyl-7-(sulfonylamino)-1H-indoles (VI).