Barluenga reagent

Bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate

Bis(collidine)iodine(I) hexafluorophosphate

CAS#113119-46-3, 1253697-29-8

Structure:

Reaction scheme:

Bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate is a new Barluenga’s reagent we developed recently. It has greater ionic character than normal Barluenga’s reagent-Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4; CAS  15656-28-7).

According to the recent study, Bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate is used in the synthesis of Diindenopyrenes: Extended 1,6- and 1,8-Pyrenoquinodimethanes with Singlet Diradical Characters. Diindenopyrene and its diastereomer, which are extended homologues of 1,6- and 1,8-pyrenoquinodimethanes fused by indene units, respectively, were synthesized by reaction of 1,4,5,8-tetrakis(mesitylethynyl)naphthalene with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate via cationic cyclization mechanisms at both centers of reaction. And like other tetracyano derivatives which were studied intensively from a viewpoint of electron acceptors in organic (semi)conductors, we expect such new extended 1,6- and 1,8-Pyrenoquinodimethanes derivatives will perform better.

Remark: Barluenga’s reagent is an iodinating and oxidizing reagent applied in all kinds of unsaturated substrates such as isolated and conjugated olefins, acetylenes and aromatic compounds tolerating a variety of functional groups. The reagent is conveniently prepared by reaction of HgO/HBF4 -SiO2 or AgBF4-SiO2 with iodine and pyridine in CH2Cl2.