Abstract
A series of new monoligated arylpalladacyclic complexes with amide, urea, and carbamate frameworks have been developed and were found to be highly active for Suzuki–Miyaura cross-couplings. These palladacycle precatalysts are derived from simple, inexpensive starting materials and are air- and moisture-stable. The most active congeners among those tested are the urea-based palladacycles, which in conjunction with a tBu3P ligand induce high conversions for a range of aryl halide and boronate coupling partners. Notably, aryl chlorides are viable coupling partners even under relatively mild conditions at short reaction times (e.g., 1 h at 60 °C). One of the best catalysts described here exhibits improved turnover frequency for a particularly difficult coupling reaction involving an aryl chloride and a sterically congested boronic ester.
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