Abstract
A Pd-catalyzed domino reaction of 1,8,13-tribromo-9-methoxytriptycenes is reported. Under conventional Suzuki coupling conditions, the triptycenes underwent multiple transformations to give 1,9-bridged triptycenes. Based on mechanistic investigations, a single Pd catalyst functions as Pd0, PdII and PdIV species to catalyze four distinct processes: 1) aryl-to-alkyl 1,5-Pd migration, 2) intramolecular arylation, 3) homocoupling of phenylboronic acid and 4) Suzuki coupling. More information can be found in the Communication by T. Iwata, M. Shindo et al. (DOI: 10.1002/chem.202101728).
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