Abstract A method for the direct and rare umpolung of the 3 position of indoles is reported. The activation of N-acetylindole with iron (III) chloride allows the C [BOND] H addition of aromatic and heteroaromatic substrates to the C2 [DOUBLE BOND] C3 double bond of the indole nucleus to generate a quaternary center at C3 and leads regioselectively to 3- arylindolines. Optimization, scope (50 examples), practicability (gram scale, air ...