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

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 toler...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2489-2498
Main Authors: Yilmaz, Ozgur, Dengiz, Cagatay, Emmert, Marion H
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02642