15656-28-7

Bis(pyridine)iodonium tetrafluoroborate is iodinating agent for the selective functionalization of unsaturated compounds; can also mediate C-C bond formation.

Bis(pyridine)iodonium tetrafluoroborate is prepared by the reaction of HgO/HBF4-SiO2 with iodine and pyridine in dry CH2Cl2 at rt. Solids are filtered off, and the reagent is isolated by precipitation from CH2Cl2 solution by addition  of cold ether, repeating the operation several times until a negative test for mercury(II) is obtained (i.e. absence of precipitation of mercury by treatment of an aliquot with NaBH4/NaOH).

Yellow powder

Bis(pyridine)iodonium tetrafluoroborate is used as mild iodinating and oxidizing reagent. It is also useful for selective iodination of free phenolic groups in tyrosine residues during solid-phase synthesis.

Iodination and oxidation reagent.

reagent type: oxidant

Bis(pyridine)iodonium tetrafluoroborate can be safely stored under a nitrogen atmosphere (in the dark at 4 °C)  for long periods of time (up to 3 months has been observed) without changing either properties or physical  appearance.

recrystallization from CH2Cl2-CHCl3 (white solid)