A method for the synthesis of dihydrodibenzo[c,e]azocine derivatives via a regioselective intramolecular aminoiodination of alkynes under visible light irradiation has been developed. This protocol uses a combination of iodine and hypervalent iodine to realize a sulfonamidyl radical, followed by intramolecular addition to alkyne to form a vinyl radical. Subsequent trapping of iodine radical affords an 8-membered heterocycle. Applications of the obtained iodinated 8-membered heterocycles in the Suzuki-Miyaura coupling and deiodination are also demonstrated. (Figure presented.).
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