Hydrated nickel (Ⅱ) halides mediated ring opening reaction with N-tosylaziridines

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An efficient and water tolerant method for the synthesis of β-haloamines is described utilizing hydrated nickel (Ⅱ) halides (NiX2·nH2O X =Cl,Br,Ⅰ) and aziridines as starting materials.N-Tosylaziridines reacted with NiCl2·6H2O or NiI2·6H2O givingβ-chloro- or β-iodoamines in high yields (73-99%) within a short time,but 10 mol% of n-Bu4NBr should be added in the reactions of N-tosylaziridines with NiBr2·3H2O in order to obtain the high yields of correspondingβ-bromoamines.Solvent played an important role in the reactions.The proper solvent for the reaction of NiCl2·6H2O was DMF,while NiBr2·3H2O or NiI2·6H2O proceeded well in 1,4-dioxane.
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