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Transition‐Metal‐Free Matsuda‐Heck Type Cross‐Coupling and Mechanistic Evidence for a Radical Mechanism
Journal article   Open access   Peer reviewed

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

Julien Bergès, Yassir Zaid, Anis Tlili, Jean-Marc Sotiropoulos and Marc Taillefer
European Journal of Organic Chemistry, Vol.2021(10), pp.1559-1563
12/03/2021

Abstract

Arylation Csp2−Csp2 bond formation Matsuda-Heck Reaction mechanisms Stilbene
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.
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