Mechanistic Insights into CN Coupling Catalyzed by 1,3-Diketonate-Ligated Copper: Unprecedented Activation of Aryl Iodide

The mechanism of CN cross‐coupling reactions catalyzed by CuI associated to a 1,3‐diketonate ligand L− is investigated by cyclic voltammetry and 1H NMR spectroscopy up to the formation of the key anionic complex [LCuINHCy]−. Its reaction with PhI, shown experimentally, proceeds via an unusual iodid...

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Bibliographic Details
Published in:ChemCatChem 2011-02, Vol.3 (2), p.305-309
Main Authors: Franc, Grégory, Cacciuttolo, Quentin, Lefèvre, Guillaume, Adamo, Carlo, Ciofini, Ilaria, Jutand, Anny
Format: Article
Language:English
Subjects:
copper
CN coupling
density functional calculations
electrochemistry
ketones
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Summary:The mechanism of CN cross‐coupling reactions catalyzed by CuI associated to a 1,3‐diketonate ligand L− is investigated by cyclic voltammetry and 1H NMR spectroscopy up to the formation of the key anionic complex [LCuINHCy]−. Its reaction with PhI, shown experimentally, proceeds via an unusual iodide activation, and the transition states are investigated by density functional calculations.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201000230