The halogenation of organic molecules is one of the most common methods for the functionalization of substrates, as halogen atoms often serve as good handles for further chemical manipulations, like e.g., substitution and cross coupling reactions. In addition, halogenated compounds play an important role as pharmaceuticals, agrochemicals, and materials. Electrophilic halogenation of alkenes constitutes the oldest and still most frequently used procedure to introduce halogen atoms into a molecule. Despite the broad application of halogenated compounds, common strategies for the formation of carbon-halogen bonds often suffer from severe drawbacks such as stereo- and regioselectivity issues as well as from environmental and/or safety concerns. Our research addresses these problems by taking Nature as an inspiration and imitating its concepts of halide umpolung employing hypervalent iodane reagents and catalysts. Mild, generally applicable, and selective methods for the formation of carbon-halogen bonds are thus established. Utilizing these methods, a rich diversity of novel chemical structures is obtained that are often not accessible by standard methods. Our recent advances in developing novel halogenation strategies, in particular for fluorinations, chlorinations and brominations of alkenes, will be discussed.

New halogenation strategies for the generation of unusual reactivities and selectivities

255th National Meeting (2018)

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