An Iodine-catalysed process for an efficient and scalable sulfenylation protocol for indoles employing aryl-/alkyl sulfonyl chlorides has been developed. A series of sterically and electronically divergent aryl-/alkyl sulfonyl chlorides participated in the sulfenylation of C(sp2)–H bonds, resulting in a high to excellent yield of indole 3-sulfenylether molecules. It is noteworthy that indole-3-thiomethyl