ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H‑hydronaphthalene and chromene) and 2H‑Quinoline Bearing an Alkenyl Iodide Moiety

Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.