Halogen bonds are attractive non-covalent interactions between electrophilic halogen substituents (bound to electronegative backbones) and Lewis bases.The aim of our investigations is to develop applications for multidentate halogen bond donors in organic synthesis. Since it is well known that halides as Lewis bases form strong halogen bonds in the solid state, we sought to use strong halogen bond donors for the abstraction of halide leaving groups from organic substrates. Recently we could demonstrate that cationic halogen bond donors are able to activate the carbon-bromine bond of benzhydryl bromide and related substrates.[1,2] Comparative experiments provide strong indications that the activation can be ascribed to halogen-bonding.References:[1] S. M. Walter, F. Kniep, E. Herdtweck, S. M. Huber, Angew. Chem. Int. Ed. 2011 , 50, 7181.[2] F. Kniep, L. Rout, S. M. Walter, H. K. V. Bensch, S. H. Jungbauer, E. Herdtweck, S. M. Huber, Chem. Commun. 2012 , 48, 9299.

Carbon-halogen bond activation by halogen bond donors

245th National Meeting (2013)

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