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Transition‐Metal‐Free Matsuda‐Heck Type Cross‐Coupling and Mechanistic Evidence for a Radical Mechanism
Author(s) -
Bergès Julien,
Zaid Yassir,
Tlili Anis,
Sotiropoulos JeanMarc,
Taillefer Marc
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100032
Subject(s) - chemistry , palladium , transition metal , heck reaction , catalysis , photochemistry , combinatorial chemistry , coupling (piping) , mechanism (biology) , polymer chemistry , organic chemistry , epistemology , engineering , mechanical engineering , philosophy
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.