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

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.

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Bibliographic Details
Published inSynlett no. 4; pp. 592 - 596
Main Authors Zhu, Mingzhao, Jalalian, Nazli, Olofsson, Berit
Format Journal Article
LanguageEnglish
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
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2008-1032050