In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C–N Bond Formation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ACS Catalysis Année : 2022

In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C–N Bond Formation

Résumé

We report an efficient Buchwald-Hartwig cross-coupling reaction in alcoholic solvents, in which low catalyst loading showed excellent performance for coupling aryl halides (I, Br, Cl) with a broad set of amines, amides, ureas, or carbamates under mild conditions. Mechanistically speaking, in protic and polar medium, extremely bulky biarylphosphine ligands interact with dimeric precatalyst [Pd(π-Rallyl)Cl]2 to form the corresponding cationic complexes [Pd(π-Rallyl)(L)]Cl in situ and spontaneously. The resulting precatalyst further evolves under basic conditions into the corresponding L-Pd(0) catalyst, which is commonly employed for cross-coupling reactions. This mechanistic study highlights the prominent role of alcoholic solvents for the formation of the active catalyst.
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hal-03546107 , version 1 (27-01-2022)

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Paternité - Pas d'utilisation commerciale - Pas de modification

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Philippe Steinsoultz, Aurélien Bailly, Patrick Wagner, Estefania Oliva, Martine Schmitt, et al.. In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C–N Bond Formation. ACS Catalysis, 2022, 12 (1), pp.560-567. ⟨10.1021/acscatal.1c04641⟩. ⟨hal-03546107⟩
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