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Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

L. Reginald Mills, Joshua M. Graham, Purvish Patel and Sophie A. L. Rousseaux*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada, Email:

L. R. Mills, J. M. Graham, P. Patel, S. A. L. Rousseaux, J. Am. Chem. Soc., 2019, 141, 19257-19262.

DOI: 10.1021/jacs.9b11208

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A Ni-catalyzed reductive coupling enables the synthesis of benzonitriles in good yields from aryl (pseudo)halides and 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions.

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proposed mechanism

Key Words

cyanation, zinc

ID: J48-Y2019