Copper-Catalyzed Electrophilic Amination: An Umpolung Strategy for New C–N Bond Formations

The nitrogen atom is ubiquitous in bioactive molecules and functional materials, and the development of new C–N bond forming strategies is thus one of the long-standing research subjects in the synthetic community. This account describes the nitrogen-umpolung-enabled copper-catalyzed highly chemo- a...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 96; no. 3; pp. 198 - 207
Main Author Hirano, Koji
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 15.03.2023
Chemical Society of Japan
SeriesThe Chemical Society of Japan Award for Young Chemists for 2015
Subjects
Alkenes
Alkylamines
Amines
Copper
Enantiomers
Functional materials
Nitrogen
Organosilicon compounds
Stereoselectivity
Substrates
Amination
Copper
Umpolung
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Summary:The nitrogen atom is ubiquitous in bioactive molecules and functional materials, and the development of new C–N bond forming strategies is thus one of the long-standing research subjects in the synthetic community. This account describes the nitrogen-umpolung-enabled copper-catalyzed highly chemo- and stereoselective amination protocols developed by the author’s research group. Starting from the C–H amination, electrophilic amination of stable organoboron and organosilicon compounds, aminoboration/hydroamination of alkenes, and their applications to the synthesis of functionality-rich alkylamines are shown. The reaction design, concept, and substrate scope are briefly summarized.
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ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20230003