116503-57-2Relevant articles and documents
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.
A High-Yield Regiospecific Synthesis of Keto Oximes from Aryl-Conjugated Ethylenes and Ethyl Nitrite in the Presence of Cobalt Complex and BH4- Ion
Okamoto, Tadashi,Kobayashi, Kenji,Oka, Shinzaburo,Tanimoto, Shigeo
, p. 4897 - 4901 (2007/10/02)
The title reaction of substituted styrenes, 1-phenyl-1,3-butadiene, and some cyclic aryl-conjugated ethylenes proceeds smoothly at room temperature, affording the corresponding oximes in moderate to nearly quantitative yields.The reaction mechanism is discussed on the basis of the formation of an alkylcobalt intermediate and its subsequent reaction with ethyl nitrite.
