This report describes the synthesis of model complexes for key intermediates in the Pd-catalyzed transannular C(sp3)–H arylation of alicyclic amines. These complexes react stoichiometrically with phenyl iodide to afford C–H arylation products. Furthermore, they participate in H/D exchange with d10-tert-butanol at temperatures as low as 40 °C. Overall, these studies provide insights into the factors controlling transannular C(sp3)–H activation in these systems.
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