A series of palladium based oxidative addition complexes containing phosphines and aryl halides were synthesized as new effective precatalysts and applied for sensitive Suzuki-Miyaura cross coupling reactions at ambient conditions. This protocol is compatible with sensitive functional groups indicating an improved alternative to previously developed analogous classes of precatalysts by simply mixing the sensitive phosphine ligands with air sensitive palladium precursors to form presumed well-defined monoligated species. The obstruction of the catalytic reaction by functional complexity including sensitive ligand/metal optimization and longer activation time can be avoided by these preformed catalysts. These easily prepared and remarkably air stable oxidative addition complexes are also highly effective precatalyst for Pd-catalyzed cross coupling of hindered, electron-deficient anilines with hindered (hetero)aryl bromides and chlorides.

More than just a ligand: A powerful oxidative addition catalyst system for sensitive cross coupling reaction

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ACS Fall 2022

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