Iodonium metathesis reactions of unreactive aryl iodides

Author:

Racicot Léanne,Ciufolini Marco A.

Funder

University of British Columbia

Canada Research Chair Program

NSERC

CFI

BCKDF

Vanier Foundation

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference47 articles.

1. Iodonium Metathesis Reactions

2. Related reactions include the exchange of oxygen ligands between PhI(OH)OTs and an aryl iodide and of aryl ligands between two diaryilodonium triflates:

3. [ Hydroxy(tosyloxy)iodo]benzene, a versatile reagent for the mild oxidation of aryl iodides at the iodine atom by ligand transfer

4. Fluoride-promoted ligand exchange in diaryliodonium salts

5. The original disclosure (ref. 1) indicated that 4-bromo-iodobenzene would not react with Ph2IOTf. In fact, metathesis does occur upon prolonged heating with freshly prepared and recrystallized Ph2IOTf (earlier experiments were carried out with commercial, non-recrystallized material). Recrystallization of the diaryliodonium triflates as described herein produces more consistent results, both in terms of kinetics and of yield.

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