25786-67-8Relevant academic research and scientific papers
Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of Δ2-Isoxazolines from Oximes
Shi, Di,Qin, Hai-Tao,Zhu, Chen,Liu, Feng
supporting information, p. 5084 - 5088 (2015/08/18)
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 Δ2-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. The title reaction involves Selectfluor-Bu4NI-mediated C-O bond formation in aqueous media under metal-free conditions. A variety of Δ2-isoxazolines are directly synthesized from oximes by remote intramolecular functionalization of C(sp3)-H bonds.
