Transition-State Metal Aryl Bond Stability Determines Regioselectivity in Palladium Acetate Mediated C–H Bond Activation of Heteroarenes

Abstract

Density functional calculations reveal that the stability of developing metal aryl bonds in Pd(II)-acetate C-H activation transition states determines regioselectivity in arene and heteroarene compounds. This kinetic-thermodynamic connection explains the general preference for activation of the strongest C-H bond and provides the possibility for regioselectivity prediction.