Regioselective difunctionalization of alkene: A simple access to haloether, haloesters and halohydrins

We have demonstrated a protocol to generalize regioselective 1,2-difunctionalization of alkenes, which is a simple and efficient method for the preparation of haloethers, haloesters and halohydrins using alcohol as nucleophiles with inexpensive and commercially available N-halosuccinimide (NXS) as the halogenating reagent with low catalyst loading under mild reaction condition. The methodology is also applicable for the easy access of various alkenes such as terminal, internal, heterocyclic ones and cyclic endoene with the striking features of high product yields (up to 99%). Moreover, a bioactive molecule was employed as substrate to test this reaction, the corresponding products were successfully prepared with moderate to good yield without losing their ester functional group. The given protocol has the following advantages such as a direct difunctionalization of alkenes, operational simplicity, good functional group tolerance and a wide substrate scope.