Mechanical‐Force‐Driven Radical Cross‐Coupling of Aryl Diazonium Salts with Nitroalkenes

An unprecedented mechanical‐force‐induced cross‐coupling of aryl diazonium salts with nitroalkenes has been developed under transition‐metal‐free ball‐milling conditions. This process utilizes readily available sodium chloride (NaCl) as an efficient activator, enabling the cleavage of the CN bond in aryldiazonium salts to generate aryl radicals. These radicals are subsequently trapped by nitroalkenes, leading to the formation of stilbene derivatives. The protocol is notable for its solvent‐free and transition metal‐free synthesis, straightforward operation, broad scope, and exclusive selectivity for the (E)‐configuration of the resulting stilbenes.