Abstract A metal‐free hypervalent iodine‐mediated C3‐trifluoropropionyloxylation of N ‐substituted indoles was developed. (Bis‐trifluoropropanoate)iodobenzene was used as both the oxidant and fluorine source. The reaction was sensitive to the N ‐protecting groups of the indoles. N ‐acylated indoles provided 3‐trifluoropropionyloxylated indoles, while 3‐trifluoropropionyloxylated oxindoles were generated from indoles bearing N ‐alkyl groups.