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Iron-Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines

Ozgur Yilmaz*, Cagatay Dengiz and Marion H. Emmert*

*Department of Chemistry, Mersin University, 33343 Mersin, Turkey; Merck, 770 Sumneytown Pike, West Point, Pennsylvania 19486, United States, Email: yilmazozgurmersin.edu.tr, marion.emmertmerck.com

O. Yilmaz, C. Dengiz, M. H. Emmert, J. Org. Chem., 2021, 86, 2489-2498.

DOI: 10.1021/acs.joc.0c02642



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Abstract

A mild protocol for the α-C-H cyanation of tertiary aliphatic, benzylic, and aniline-type substrates and complex substrates tolerates a broad range of fuctional groups, including various heterocycles and ketones, amides, olefins, and alkynes. The presented catalyst system especially tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway.


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Examples of Complex Amines and Drug Substrates

proposed mechanism



Key Words

α-Aminonitriles, Peresters


ID: J42-Y2021