Synthesis of Functionalized Monoaryl-λ³-iodanes via Chemo- and Site-selective ipso-Substitution Reactions.

Monoaryl-λ³-iodanes are potentially attractive arylating agents. They are generally synthesized from aryl iodides via oxidation, which can cause functional group incompatibility, especially when polyfunctionalized derivatives are desired. Here we describe the direct synthesis of monoaryl-λ³-iodanes via a chemoselective ipso-substitution reaction of arylgermanes and arylstannanes with iodine tris(trifluoroacetate). The generated iodanes were converted to iodonium ylides or used for further transformations in one pot. The presented method enables the preparation of polyfunctionalized monoaryl-λ³-iodanes.