Synthesis of Bridged Bicyclic Amines by Intramolecular Amination of Remote C–H Bonds: Synergistic Activation by Light and Heat

The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C–H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by densi...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (16), p.6578-6583
Main Authors: Lux, Michaelyn C, Jurczyk, Justin, Lam, Yu-hong, Song, Zhiguo J, Ma, Chao, Roque, Jose B, Ham, Jin Su, Sciammetta, Nunzio, Adpressa, Donovon, Sarpong, Richmond, Yeung, Charles S
Format: Article
Language:English
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Summary:The construction of complex aza-cycles is of interest to drug discovery due to the prevalence of nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C–H amination approach to afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory and nuclear magnetic resonance investigations, we determined the unique roles of light and heat activation in the bicyclization mechanism. We applied both light and heat activation in a synergistic fashion, achieving gram-scale bridged aza-cycle synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02345