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A convenient method for the rapid construction of indolo[2,3-b]indoles has been developed. This cascade reaction involving condensation, dehydroaromatization, and oxidative annulation was achieved in a one-pot TMSI/DMSO system, providing a diversity of functionalized indolo[2,3-b]indoles in satisfactory yields under facile metal-free conditions. The present protocol provides a straightforward approach to access structurally valuable indolo[2,3-b], indoles.