Issue 30, 2022

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.

Graphical abstract: Decyanation–(hetero)arylation of malononitriles to access α-(hetero)arylnitriles

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Communication
Submitted
03 fev 2022
Accepted
15 mar 2022
First published
15 mar 2022

Org. Biomol. Chem., 2022,20, 5933-5937

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

L. R. Mills, P. Patel and S. A. L. Rousseaux, Org. Biomol. Chem., 2022, 20, 5933 DOI: 10.1039/D2OB00236A

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