Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism

The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 degrees C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Automated summary

The Matsuda-Heck reaction, typically carried out with palladium catalysts, has been successfully done under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This study demonstrates a selective and direct synthesis of stilbenes from aryldiazonium salts at mild temperature, with mechanistic studies suggesting a radical pathway initiated by DMF.