Abstract
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.
Original language | English |
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Article number | e202412247 |
Journal | Angewandte Chemie International Edition |
Volume | 63 |
Issue | 51 |
Number of pages | 9 |
ISSN | 1433-7851 |
DOIs | |
Publication status | Published - 16 Dec 2024 |
Keywords
- Carbon isotope labeling
- Carbonylation
- Catalysis
- Ketones
- Nickel