Synthesis of iodonium salts and related compounds

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Recent Literature

A new, regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations, is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.
M. Bielawski, D. Aili, B. Olofsson, J. Org. Chem., 2008, 73, 4602-4607.

A simple and easy method for the synthesis of various iodonium salts involves the reaction of potassium organotrifluoroborates with p-iodotoluene difluoride under mild conditions.
T. Fukuhara, C. Hasegawa, S. Hara, Synthesis, 2007, 1542-1546

A direct synthesis of symmetric and unsymmetric electron-rich diaryliodonium salts delivers diaryliodonium tosylates in high yields using MCPBA and toluenesulfonic acid. An in situ anion exchange has also been developed, giving access to the corresponding triflate salts.
M. Zhu, N. Jalalian, B. Olofsson, Synlett, 2008, 592-596.

Phenyliodonium ylides provide easy access to various 1,1-cyclopropane diesters using rhodium or copper catalysis and are safer and convenient alternatives to the corresponding diazo compounds. Moreover, the iodonium ylide of dimethyl malonate was obtained in 78% yield using improved conditions that involve a simple filtration step to isolate the desired product.
S. R. Goudreau, D. Marcoux, A. B. Charette, J. Org. Chem., 2009, 74, 470-473.