Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines

Abstract

A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes including derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.

Syntheses of Benzo[b]furan-6-carbonitrile and 6-Cyanobenzo[b]furan-2-boronic Acid Pinacol Ester

“…[14] One notable exception was 2,4,6-triiodo-3-hydroxybenzaldehyde, in which the iodo group para to the aldehyde was maintained (Scheme 1). …”

Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams

“…After 2 h, signals of the monoiodo azetidinone 6 appeared, and, after 12 h, the conversion to 6 was complete, thus supporting the action of TEA on 5 as a deiodinating agent. [15] TEA is thus responsible for the increased amount of the monoiodo compound. To confirm this finding, diiodoazetidinone 5 (13 mg, 26 µmol) was treated with TEA (7.2 µL, 2 equiv.)…”

Flavoprotein Iodotyrosine Deiodinase Functions without Cysteine Residues

“…Accordingly, the chemical and biochemical precedence for promoting reductive dehalogenation by cysteine and related selenocysteine derivatives is irrelevant to IYD. A recent report indicates that certain amines may also promote reductive dehalogenation in a model system related to those containing cysteine,19 and therefore the role of histidine and lysine residues in IYD also deserves scrutiny. Interestingly, an expected intermediate of such a process, lysine‐εNH‐Cl, has just been proposed to form during catalysis of the reverse process, a flavin‐dependent halogenation 20.…”