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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, * 
* Corresponding author
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
Abstract : 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
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Submitted on : Sunday, November 28, 2021 - 3:51:20 PM
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CNRS | UNIV-PAU | UNIV-LYON1 | INSA-LYON | ICG | IPREM | INC-CNRS | CHIMIE | UNIV-MONTPELLIER | IPREM-CAPT | ICBMS | INSA-GROUPE | UDL

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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, Wiley-VCH Verlag, 2021, 2021 (10), pp.1559-1563. ⟨10.1002/ejoc.202100032⟩. ⟨hal-03162580⟩

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