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Transnitrilation from Dimethylmalononitrile to Aryl Grignard and Lithium Reagents: A Practical Method for Aryl Nitrile Synthesis

Jonathan T. Reeves*, Christian A. Malapit, Frederic G. Buono, Kanwar P. Sidhu, Maurice A. Marsini, C. Avery Sader, Keith R. Fandrick, Carl A. Busacca and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email:

J. T. Reeves, C. A. Malapit, F. G. Buono, K. P. Sidhu, M. A. Marsini, C. A. Sader, K. R. Fandrick, C. A. Busacca, C. H. Senanayake, J. Am. Chem. Soc., 2015, 137, 9481-9488.

DOI: 10.1021/jacs.5b06136

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The commercially available, bench-stable dimethylmalononitrile (DMMN) enables an electrophilic cyanation of aryl Grignard or lithium reagents, generated in situ from the corresponding aryl bromides or iodides. The transnitrilation with DMMN avoids the use of toxic reagents and transition metals and occurs under mild reaction conditions, even for extremely sterically hindered substrates.

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Key Words


ID: J48-Y2015