Decyanation-(hetero)arylation of malononitriles to access α-(hetero)arylnitriles.

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.