Introduction: This Dataverse entry contains supporting data for our journal article “Nickel Catalyzed Carbonylative Cross Coupling for Direct Access to Isotopically Labeled Alkyl Aryl Ketones” submitted for review. The dataset contains additional experimental and computational work performed to support the chemical process, which was not included in the manuscript. The dataset consists of two files: 1) 'Additional experimental and computational results.pdf', and 2) 'optimized_geometries_Ni.xyz'. The first file explains the experimental and computational techniques employed and the analysis to support the chemical reaction. The second file contains the XYZ structures of the computationally optimized geometries in the work.

Abstract from article: Here we present an effective nickel-catalyzed carbonylative cross-coupling for direct access to alkyl aryl ketones from readily accessible redox-activated tetrachlorophthalimide esters and aryl boronic acids. The methodology, which is run employing only 2.5 equivalents of CO and simple Ni(II) salts as the metal source, exhibits a broad substrate scope under mild conditions. Furthermore, this carbonylation chemistry provides an easy switch between isotopologues for stable (13CO) and radioactive (14CO) isotope labeling, allowing its adaptation to the late-stage isotope labeling of pharmaceutically relevant compounds. Based on DFT calculations as well as experimental evidence, a catalytic cycle is proposed involving a carbon-centered radical formed via nickel(I)-induced outer-sphere decarboxylative fragmentation of the redox-active ester.

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