The synthesis of monocyclic, spirocyclic and fused bicyclic secondary amines bearing a gem‐difluorocyclopropane moiety via difluorocyclopropanation of unsaturated N‐Boc derivatives using the trifluoromethyl(trimethyl)silane/sodium iodide [CF3SiMe3‐NaI] system is described. The relative order of the substrate reactivity is established. It is shown that for the reactive alkenes the standard reaction conditions can be used, whereas for the substrates with low reactivity, slow addition of the Ruppert–Prakash reagent is necessary.magnified image

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