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  • Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenonesand Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulationof Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles
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  • 2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones andpolycyclic aromatic ketones in very good to excellent yields. This reaction represents one of thefirst examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond ofa nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, aswell as a model accounting for the electronic effects of substituents on the aromatic ring of thenitrile, is proposed.
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