Mild, metal-free, highly regioselective hypervalent-iodine mediated C-2 acetoxylation and C-3 oxidations of N-substituted indoles with (diacetoxyiodo)benzene [PhI(OAc)] have been reported. The reaction involves three cascade steps. The quantity of PhI(OAc) employed in this reaction plays a key role in the outcome of three types of products (2a-4a). Furthermore, the mild and highly regioselective C-2 oxidation and C-3 dichlorination of N-substituted indoles with PhICl have been developed. Extensive studies including in situ IR techniques and HO-labeling experiment were performed to gain insight into the possible reaction mechanism.
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