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

Date

2021-01-19

Author

Yilmaz, Ozgur
Dengiz, Çağatay
Emmert, Marion H

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This manuscript details the development of a general and mild protocol for the α-C–H cyanation of tertiary amines and its application in late-stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates and complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles and ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C–H cyanation frequently occur via free radical mechanisms and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described catalyst system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.

Subject Keywords

Lipids, Purification, Amines, Mixtures, Solvents

URI

https://hdl.handle.net/11511/88582

Journal

The Journal of organic chemistry

DOI

https://doi.org/10.1021/acs.joc.0c02642

Collections

Department of Chemistry, Article

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Citation Formats

O. Yilmaz, Ç. Dengiz, and M. H. Emmert, “Iron-Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines.,” The Journal of organic chemistry, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/88582.