Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 4, Pages 2036-2039Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja211600g
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Funding
- University of Illinois
- NSF
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A highly selective C-H amination reaction under iron catalysis has been developed. This novel system, which employs an inexpensive, nontoxic [(FePc)-Pc-III] catalyst (typically used as an industrial ink additive), displays a strong preference for allylic C-H amination over aziridination and all other C-H bond types (i.e., allylic > benzylic > ethereal > 3 degrees > 2 degrees >> 1 degrees). Moreover, in polyolefinic substrates, the site selectivity can be controlled by the electronic and steric character of the allylic C-H bond. Although this reaction is shown to proceed via a stepwise mechanism, the stereoretentive nature of C-H amination for 3 degrees aliphatic C-H bonds suggests a very rapid radical rebound step.
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