An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides.

A direct transformation of ortho-alkynylated aromatic vinyl ethers to 1-iodonaphthalenes and other iodo-heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope makes this work an attractive avenue towards the construction of aromatic iodides.