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Dearomative Dual-Functionalization of Aryl Iodanes.

This paper describes an unprecedented dearomatization protocol that enables the first dearomatization of aryl iodanes via a "rearrangement/addition" sequence. The process consists of two stages. First, a rapid [3,3]-sigmatropic rearrangement of aryl iodane with α-stannyl nitrile affords a highly electrophilic dearomatized intermediate at -78 °C. The low-temperature rearrangement allows for the low-temperature trapping of the in situ generated unstable dearomatized specie with various nucleophiles. As a consequence, the reaction not only breaks the aromaticity of aryl iodane but also sequentially installs two different functional groups, resulting in poly-substituted alicyclic product.