Triiodoisocyanuric acid: a new and convenient reagent for regioselective iodination of activated arenes

Abstract

O ácido triiodo-isocianúrico (TICA) foi preparado em 90% de rendimento a partir do aquecimento do ácido tricloro-isocianúrico com iodo em um tubo selado. A reação do TICA com arenos ativados em acetonitrila gera regiosseletivamente os respectivos iodo-arenos em 73-93% de rendimento isolado. Anilina e fenol também são monoiodados seletivamente usando MeOH (53%) e CH 2 Cl 2 (88%) como solventes, respectivamente. Triiodoisocyanuric acid (TICA) was prepared in 90% yield by heating trichloroisocyanuric acid with iodine in a sealed tube. The reaction of TICA with activated arenes in acetonitrile led to an efficient and highly regioselective formation of the corresponding iodoarenes, in 73-93% isolated yield. Aniline and phenol are monoiodinated regioselectively using MeOH (53%) and CH 2 Cl 2 (88%) as solvents, respectively.

Superelectrophilic Iodination of Deactivated Arenes with Triiodoisocyanuric Acid

“…Triiodoisocyanuric acid (TICA, Figure 2), was recently reported by us as an efficient reagent for the co-iodination of alkenes with oxygenated nucleophiles, 9 and the iodination of activated arenes. 10 In addition, TICA has the advantage of transferring three equivalents of iodine atom to the substrate, that is of up to 75% of its mass. As an extension of our search for more potent and practical electrophilic halogenation reagents, 11 in the present work we describe our results on the iodination of deactivated aromatic rings using triiodoisocyanuric acid in acidic medium, as the source of superelectrophilic iodine.…”

Reaction of trihaloisocyanuric acids with alkynes: an efficient methodology for preparation of β-haloenol acetates

“…8 Mixed trihaloisocyanuric acids are also known. 9,10 All these reagents have been shown to be very efficient halenium (X + ) releasing agents in diverse reactions, affording good to excellent yields of the desired halogenated products. Therefore, depending on the nature of the nucleophile reacting with these electrophilic agents, different products can be obtained, such as haloarenes, halohydrins, halocarbonyls, etc.…”

A mild and simple iodination of phenols with trichloroisocyanuric acid/ I2 /Wet SiO2 system

“…Direct iodination methods have been reported using various iodonium donating systems, such as NIS-CF 3 SO 3 H, 5 iodine-Ag 2 SO 4 , 6 iodine-HgO, 7 NIS, 8 iodinetetrabutylammonium peroxydisulfate, 9 n-BuLi-CF 3 CH 2 I, 10 ICl, 11 and triiodoisocyanuric acid. [12][13][14] However, most of these methods require toxic and costly reagents, high temperatures and long reaction times. Thus it is desirable to apply a simple, inexpensive and non-toxic reagent system for iodination of aromatic compounds.…”