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Ate complexes have been used for selective carbon-carbon bond forming reactions, however access to ate complexes with electrophilic functional groups has been limited. Main reason for the limitation lies on the preparative method of ate complexes, which includes usage of highly reactive organolithium and organomagnesium reagents. In order to develop a new strategy for the preparation of ate complexes directly from other ate complexes, we investigated halogen-metal exchange reactions of organic halides with ate complexes. The metalation is considered to be potentially chemoselective and wide spectrum of application in organic synthesis is expected. Cuprates and zincates turned out to be excellent metalating reagents of functionalized aryl and alkyl halides. Some chemoselective transformations were achieved using the metalation with ate complexes and modified zincates showed very specific reactivity toward intramolecular epoxide opening reaction.

Chemoselective Metalation of Functionalized Organic Halides Using Ate Complexes.