Copper‐Catalyzed Double N‐Vinylation of Aromatic Amines: An Efficient Synthesis of Various Substituted N‐Arylpyrroles

A simple and efficient approach to various substitutedN‐arylpyrroles has been developed. The method is based on the copper‐catalyzed sequential inter‐ and intramolecular N‐vinylation of aromatic amines. The reactions proceed to afford substituted N‐arylpyrroles in good‐to‐excellent yields using CuI as the precatalyst, tBuONa as the base, and N1,N2‐dimethylethane‐1,2‐diamine (DMEDA) as the ligand. Anilines with electron‐donating and ‐withdrawing substituents as well as a heteroaromatic amine performed very well under the conditions used. Tri‐ and tetrasubstituted dienyl diiodides also performed well under the reaction conditions and afforded the corresponding substituted N‐arylpyrroles in good yields. Products were also obtained in high yields with CuBr or CuCl as precatalyst.