Proton shuttling plays an important role in metal-catalyzed reactions involving X�H (X = O, N, C) bond activation. The addition of exogenous base is often used to facilitate this process. As a consequence, all three components of the reaction mixture (catalyst, substrate, and base) must interact in order to activate the substrate. We hypothesized that incorporation of a basic functional group into the ligand framework could enhance the reactivity of Pd(II)-based catalyst systems. We have investigated a family of LX-type ligands that undergo facile proton transfer with nucleophiles in the formation of well-defined Pd(II) complexes. Fundamental studies regarding the activation of N�H bonds will be presented.

Investigation of ligand-based approaches to facilitate proton shuttling in N�H bond activation by palladium(II)

246th National Meeting (2013)

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