Ground state generation and cyclization of aminium radicals in the formation of tetrahydroquinolines

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Pratley, Cassie and Fenner, Sabine and Murphy, John A. (2024) Ground state generation and cyclization of aminium radicals in the formation of tetrahydroquinolines. Organic Letters, 26 (6). pp. 1287-1292. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.4c00179)

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Abstract

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) 3Cl 2 (42-95% yields) under acidic conditions under an air atmosphere.

  • Item type:Article
    ID code:88008
    Dates:
    Date
    Event
    16 February 2024
    Published
    2 February 2024
    Published Online
    29 January 2024
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:30 Jan 2024 17:00
    Last modified:15 Dec 2024 01:42
    URI:https://strathprints.strath.ac.uk/id/eprint/88008
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