One-pot synthesis of diaryliodonium salts using toluenesulfonic acid: A fast entry to electron-rich diaryliodonium tosylates and triflates

• Published in: Synlett no. 4; pp. 592 - 596
• Main Authors: Zhu, Mingzhao, Jalalian, Nazli, Olofsson, Berit
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 03.03.2008
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; hypervalent iodine; diaryliodonium salts; IODONIUM SALTS; IODOARENES; ALPHA-ARYLATION; IODINE; CONVENIENT; BROMIDES; oxidations; arenes; CHEMISTRY; electrophilic aromatic substitution; EXCHANGE; EFFICIENT REAGENT

A direct synthesis of symmetric and unsymmetric electron-rich diaryliodonium salts is described. The use of MCPBA and toluenesulfonic acid delivers diaryliodonium tosylates in high yields. An in situ anion exchange has also been developed, giving access to the corresponding triflate salts.