Transition‐Metal‐Free Matsuda‐Heck Type Cross‐Coupling and Mechanistic Evidence for a Radical Mechanism. Issue 10 (23rd February 2021)

• Record Type: Journal Article
• Authors: Bergès, Julien; Zaid, Yassir; Tlili, Anis; Sotiropoulos, Jean‐Marc; Taillefer, Marc
• Is Part Of: European journal of organic chemistry. Issue 10(2021)
• Page Start: 1559
• Page End: 1563
• Publication Date: 2021-02-23
• Subjects: Arylation -- Csp2−Csp2 bond formation -- Matsuda-Heck -- Reaction mechanisms -- Stilbene; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100032
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The Matsuda‐Heck reaction, usually performed with palladium catalysts, can be carried out under transition‐metal‐free conditions in the presence of a KO t Bu/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. Abstract : The Matsuda‐Heck reaction is carried out under transition metal free conditions in the presence the KO t Bu/DMF system which allows, at 20 °C, the selective and direct synthesis of stilbenes from aryldiazonium salts. Mechanistic studies suggest an overall radical process.