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

Julien Bergès (1) , Yassir Zaid (1) , Anis Tlili (2) , Jean-Marc Sotiropoulos (3) , Marc Taillefer (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
3 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

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 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Keywords: Arylation; Csp2−Csp2 bond formation; Matsuda-Heck Reaction mechanisms; Stilbene

Domains: Material chemistry; Polymers; Theoretical and/or physical chemistry; Analytical chemistry

Julien Bergès, Yassir Zaid, Anis Tlili, Jean-Marc Sotiropoulos, Marc Taillefer. Transition‐Metal‐Free Matsuda‐Heck Type Cross‐Coupling and Mechanistic Evidence for a Radical Mechanism. European Journal of Organic Chemistry, 2021, 2021 (10), pp.1559-1563. ⟨10.1002/ejoc.202100032⟩. ⟨hal-03162580⟩