Ground State Generation and Cyclization of Aminium Radicals in the Formation of Tetrahydroquinolines

This paper reports the first examples of ground state radical-mediated intramolecular C–H amination to afford 1-methyl-1,2,3,4-tetrahydroquinolines from N-2,4-dinitrophenoxy derivatives of arylpropylamines. Whereas the photoactivation of N-2,4-dinitrophenoxyamines for intermolecular reactions has be...

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Bibliographic Details
Published in:Organic letters 2024-02, Vol.26 (6), p.1287-1292
Main Authors: Pratley, Cassie, Fenner, Sabine, Murphy, John A.
Format: Article
Language:English
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Letter
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Summary:This paper reports the first examples of ground state radical-mediated intramolecular C–H amination to afford 1-methyl-1,2,3,4-tetrahydroquinolines from N-2,4-dinitrophenoxy derivatives of arylpropylamines. Whereas the photoactivation of N-2,4-dinitrophenoxyamines for intermolecular reactions has been established, ground state chemistry provides the desired cyclization products in moderate to excellent yields using Ru­(bpy)3Cl2 (42–95% yields) under acidic conditions under an air atmosphere.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00179