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

Julien Bergès; Yassir Zaid; Anis Tlili; Jean-Marc Sotiropoulos; Marc Taillefer

doi:10.1002/ejoc.202100032

Journal articles

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

Julien Bergès Yassir Zaid Anis Tlili Jean-Marc Sotiropoulos ¹ Marc Taillefer ^{2, *}

* Corresponding author

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

2 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

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

Document type :

Journal articles

Domain :

Chemical Sciences / Material chemistry

Chemical Sciences / Polymers

Chemical Sciences / Theoretical and/or physical chemistry

Chemical Sciences / Analytical chemistry

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https://hal-univ-pau.archives-ouvertes.fr/hal-03162580
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Submitted on : Monday, March 8, 2021 - 3:33:23 PM
Last modification on : Tuesday, March 9, 2021 - 3:18:32 AM

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

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

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