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Generation of Halomethyl Radicals by Halogen Atom Abstraction and Their Addition Reactions with Alkenes

  • Robynne K. Neff
    Robynne K. Neff
    Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States
  • Yong-Liang Su
    Yong-Liang Su
    Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States
  • Siqi Liu
    Siqi Liu
    College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
    More by Siqi Liu
  • Melina Rosado
    Melina Rosado
    Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States
  • Xinhao Zhang
    Xinhao Zhang
    Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China
    More by Xinhao Zhang
  • , and 
  • Michael P. Doyle*
    Michael P. Doyle
    Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States
    *[email protected]
Cite this: J. Am. Chem. Soc. 2019, 141, 42, 16643–16650
Publication Date (Web):October 1, 2019
https://doi.org/10.1021/jacs.9b05921
Copyright © 2019 American Chemical Society

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    Abstract

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    α-Aminoradicals undergo halogen atom abstraction to form halomethyl radicals in reactions initiated by the combination of tert-butyl hydroperoxide, aliphatic trialkylamine, halocarbon, and copper(I) iodide. The formation of the α-aminoradical circumvents preferential hydrogen atom transfer in favor of halogen atom transfer, thereby releasing the halomethyl radical for addition to alkenes. The resulting radical addition products add the tert-butylperoxy group to form α-peroxy-β,β-dichloropropylbenzene products that are convertible to their corresponding β,β-dichloro-alcohols and to novel pyridine derivatives. Computational analysis clearly explains the deviation from traditional HAT of chloroform and also establishes formal oxidative addition/reductive elimination as the lowest energy pathway.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b05921.

    • General experimental procedures and detailed optimization and product analyses, experimental procedures for mechanistic analyses, computational details, references, and NMR spectra (PDF)

    • Crystallographic data for 5b (CIF)

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