Hypoiodite-Mediated Metal-Free Catalytic Aziridination of Alkenes


  • This work was supported by a research grant from the National Science Foundation (CHE-1009038).


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Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO).