The halocyclization of alkynoic compounds has emerged as a pivotal transformation in synthetic organic chemistry to prepare aromatic S-heterocycles, primarily because of the versatility and functional utility of the resulting C-X bonds. Alkyl sulfides have been considered as the most effective S-nucleophiles in halocyclization reactions (Scheme 1A). For example, Turos et al. reported a cyclization reaction by treating unsaturated benzyl sulfides with bromine or iodine. then employed this approach to synthesize tubulin-binding agents. At the same time, the synthesis of benzothiophenes using methylsulfide was reported by Larock et al. The synthesis of thiophenes through halocyclization does not only necessitate a 5-endodig cyclization process but also the subsequent oxidative aromatization of the dihydrothiophenes. An electrophilic halogenating agent that can potentially act as an oxidant has not been previously used in the one-pot halocyclization/aromatization approach to obtain thiophenes. Although Zeni et al. reported the one-pot synthesis of 3-halothiophenes from homopropargyl sufides and copper halide salts, the halogen atoms in the resulting products were confined to chlorine and bromine, and the reaction required high temperatures. Notably, the incorporation of the highly reactive iodine atom has not yet been reported. Therefore, the one-pot iodocyclization of alkynoic compounds containing S-nucleophiles, followed by oxidative aromatization is a promising method for thiophene synthesis. Our group has recently reported that thioesters are effective, rare S-nucleophiles for the halocyclization of alkenoic substrates (Scheme 1 B). The sufficient nucleophilicity of the sulfur atom in thioesters can be attributed to the mismatched orbital interactions. The corresponding alkenoic thioesters can be thus easily prepared from alcohols and halides in a single step. The halogenating agent, N-bromoacetamide (NBA), can be safely handled and the reaction proceeds even under mild conditions, unlike Br2, which is volatile and toxic. This study investigated the possibility of obtaining dihydrothiophenes by halocyclization starting from alkynoic thioesters. The one-pot synthesis of thiophenes by a subsequent oxidative aromatization by the same electrophilic halogenating agent was then assessed.