Abstract
Two 1,2,3-triazole-derived monocationic salts 3 and 4 bearing N-aryl wingtips were prepared using copper-catalyzed “click” reactions followed by alkylations with iodomethane. Employing a silver–carbene transfer method, two dinuclear palladium(II) complexes of triazolin-5-ylidenes (5/6) were obtained, the former of which has been reported previously. Bridge-cleavage reaction of 5 as a representative with PPh3 yielded cis-configured mesoionic carbene/phosphine hybrid complex cis-7 and homoleptic bis(phosphine) complex 8, suggesting the presence of a ligand exchange process. In contrast, bridge breakages of 5/6 with pyridine cleanly afforded PEPPSI-type complexes 9 and 10 in near quantitative yields. Finally, all complexes were exploited to catalyze Mizoroki–Heck coupling reactions with aryl bromides as the substrates, and PEPPSI-type complex 9 was found to be the best performer generally giving good to excellent yields.
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