What a couple! An intramolecular, C(sp3)N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural product lyconadin A. The current study employs conformationally unbiased substrates with less acidic CH bonds and less reactive nitrogen nucleophiles. ZnCl2 was identified as an important additive.