Hypervalent iodine chemistry has developed from a laboratory curiosity to a powerful tool within the last decades, often offering novel reactivities. Our group being interested in the exploration of mild and selective (catalytic) methods for the formation of carbon-halogen bonds, we focused in our latest work on the electrophilic fluorination of olefins, a still problematic transformation due to the often hampered reactivity of the established F-reagents. With bench stable fluorobenziodoxoles, a new iodine(III) fluorine-transfer reagent became available, which offers a complementary chemoselectivity to the common F-reagents thus leading to unique, fluorinated structural scaffolds. One example of such a unusual fluorination reactivity is the transformation of o-amidyl styrenes by the F-iodanes giving rise to a novel substrate class, the fluorinated benzoxazepines. The scope of the developed methodology as well as investigations on the reaction mechanism and the unexpected selectivity of this unprecedented fluorination/1,2-aryl shift/cyclization cascade will be presented.

Hypervalent iodine mediated fluorinations: Versatile tools for the exploration of novel reactivities

253rd National Meeting (2017)

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