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On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition‐Metal Complexes

Angewandte Chemie International Edition · 2012 · Vol. 51(13) · pp. 3066–3072

Eric M. Simmons(University of California, Berkeley)John F. Hartwig✉(University of California, Berkeley)

Abstract

Rate versus selectivity determining: The measurement of a kinetic isotope effect (KIE) can provide valuable information about the mechanism of a reaction, but care must be taken in the design and interpretation of KIE experiments. Depending on the experiment that is conducted, the observation of a primary KIE resulting from H/D substitution does not necessarily imply that CH bond cleavage occurs during the rate-determining step of a reaction. FG=functional group.

Asymmetric Hydrogenation and Catalysis Catalytic C–H Functionalization Methods Fluorine in Organic ChemistryKinetic isotope effectDeuteriumChemistryKinetic energyIsotopeInterpretation (philosophy)Bond cleavageComputational chemistryThermodynamicsOrganic chemistry