Mechanically Induced N ‐arylation of Amines with Diaryliodonium Salts

Diaryliodonium salts are stable and less toxic arylation reagents widely used in organic chemistry. Various N ‐arylated compounds have been prepared with diaryliodonium salts in the past decades. Taking the advantages of their superiority, herein, we have developed two novel arylation methods of amines with diaryliodonium salts by ball milling for the preparation of diarylamines. The protocols are highlighted by operational simplicity, mild conditions and broad functional group tolerance. It is found that the reaction undergoes the cross‐coupling pathway as amines milled with diaryliodonium salts in the presence of catalyst CuI. The ball milled organic reaction of amines by liquid‐assisted grinding in the absence of transition metals follows a radical mechanism.