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Updated: Sep 29, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Decyanation-(hetero)arylation of malononitriles to access α-(hetero)arylnitriles
L Reginald Mills1, Purvish Patel1, Sophie A L Rousseaux1
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada. sophie.rousseaux@utoronto.ca.
Abstract:
Quaternary α-(hetero)arylnitriles are desirable biologically relevant products, however the existing methods for their synthesis can be unselective or require the use of undesirable reagents, such as cyanide salts. Herein we report a one-pot method for transnitrilation-mediated decyanation-metalation of disubstituted malononitriles, followed by treatment with (hetero)aryl electrophiles to access quaternary α-(hetero)arylnitrile products. A number of products were prepared using this method (34 examples, 27-99% yield). This method highlights the usefulness of malononitriles as precursors for alkylnitrile-containing compounds.
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