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Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of [Delta]2-Isoxazolines from Oximes

European journal of organic chemistry, 2015-08, Vol.2015 (23), p.5084 [Peer Reviewed Journal]

ISSN: 1434-193X ;EISSN: 1099-0690 ;DOI: 10.1002/ejoc.201500780

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  • Title:
    Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of [Delta]2-Isoxazolines from Oximes
  • Author: Shi, Di ; Qin, Hai-Tao ; Zhu, Chen ; Liu, Feng
  • Subjects: Oxidation
  • Is Part Of: European journal of organic chemistry, 2015-08, Vol.2015 (23), p.5084
  • Description:   The direct functionalization of an aliphatic C-H bond within a complex molecule through a free-radical pathway is a valuable tool in synthetic chemistry. Herein, we developed an efficient transition-metal-free approach to generate [Delta]2-isoxazolines from oximes by radical-mediated C(sp3)-H oxidation. Investigation of the mechanism suggested that in the presence of Selectfluor and Bu4NI, the homolysis of the in situ formed O-I bond generated an iminoxyl radical that facilitated subsequent 1,5-H transfer and C(sp3)-H oxidation.
  • Publisher: Weinheim: Wiley Subscription Services, Inc
  • Language: English
  • Identifier: ISSN: 1434-193X
    EISSN: 1099-0690
    DOI: 10.1002/ejoc.201500780
  • Source: Alma/SFX Local Collection
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