Mn(CO)5Br‐catalyzed reaction of 1‐(2‐pyrimidyl)indoles with 1‐sulfonyl‐2‐vinylaziridines in THF in the presence of 0.25 equiv. of NaOAc affords 2‐allylated indoles in 31% to 100% yields. The protocol suits for 3‐, 4‐, 5‐, 6‐, and 7‐substituted indoles and N‐(2‐pyrimidyl)pyrroles as well as various 1‐(arylsulfonyl)‐2‐vinylaziridines such as 1‐(phenylsulfonyl)‐2‐vinylaziridine, 1‐(naphthalen‐2‐ylsulfon‐yl)‐2‐vinylaziridine, and 1‐(substituted phenylsulfonyl)‐2‐vinylaziridines. Functional groups including alkyl, alkoxy, halogen, CHO, COOMe, CF3, CN, and NO2 groups are tolerated.