Iron-Catalyzed Oxidative Monoarylation of Primary Amines with Organozinc Reagents

The reaction of a primary zinc amide with a diorganozinc reagent gives a secondary amine in the presence of Fe(acac)(3) as a catalyst and 1,2-dichloroisobutane (DCIB) as an oxidant. Halogen groups such as F, Cl, Br, and I are tolerated well. The dichloride oxidant and heat are essential to achieve the C-N bond formation presumably from a catalytic iron intermediate species bearing aryl and amido groups.