One-Pot Synthesis of Diaryliodonium Salts Using Toluenesulfonic Acid: A Fast Entry to Electron-Rich Diaryliodonium Tosylates and Triflates

Mingzhao Zhu, Nazli Jalalian, Berit Olofsson*

*Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden, Email: beritorgan.su.se

M. Zhu, N. Jalalian, B. Olofsson, Synlett, 2008, 592-596.

DOI: 10.1055/s-2008-1032050

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Abstract

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.

see article for more examples

see article for more reactions

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Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides

M. Bielawski, D. Aili, B. Olofsson, J. Org. Chem., 2008, 73, 4602-4607.

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Key Words

hypervalent iodine, diaryliodonium salts, oxidations, MCPBA, arenes, electrophilic aromatic substitution

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ID: J60-Y2008-0640