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

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:20 Nov 2024 01:27
    URI:https://strathprints.strath.ac.uk/id/eprint/88008
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