A Tutorial on Selectivity Determination in C(sp2)-H Oxidative Addition of Arenes by Transition Metal Complexes
Tyler P Pabst1, Paul J Chirik1
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Abstract:
A Tutorial on factors that determine the selectivity in C(sp2)-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp2)-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp2)-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp2)-H or C(sp2)-X (X = F, Cl, Br, I) bonds with aryl halide substrates.
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