Copper‐Catalyzed Regioselective <i>Meta</i> C─H Bond Olefination of Anilides

Herein, we report a Cu-catalyzed meta-olefination of anilides using alkenyl iodonium salts. The olefination of a panel of pivanilides was achieved using an additive-free copper-based catalytic system under mild reaction conditions (25 examples, up to 60% yield). By favoring a Heck-like four-membered transition state, the approach demonstrated an excellent regioselectivity for the meta C─H functionalization with β-styrenyl and β-alkyl-alkenyl groups using a weakly coordinated directing group (DG). Postfunctionalization reactions were conducted, highlighting both the synthetic interest of the products and the potential atom-efficiency of the process.