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From Alkenes to Isoxazolines via Copper-Mediated Alkene Cleavage and Dipolar Cycloaddition

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journal contribution
posted on 11.09.2019 by Mingchun Gao, Yuansheng Gan, Bin Xu
An unprecedented copper-mediated anion transformation is reported, along with selective CC double bond cleavage and dipolar cycloaddition reaction from simple alkenes and inexpensive copper nitrate. Various transformations demonstrate the generality of this method. Further mechanistic investigation indicates a novel ionic pathway for alkene cleavage and highlights the coeffect of iodide and boric acid as additives on the inhibition of well-documented competitive nitration byproducts.