Application of Hypervalent Iodine Compounds in Advanced Green Technologies (In Press)

Abstract

This review summarizes industrial applications of inorganic and organic polyvalent (hypervalent) iodine compounds. Inorganic iodate salts have found some application as a dietary supplements and food additives. Iodine pentafluoride is used as industrial fluorinating reagent, and iodine pentoxide is a powerful and selective oxidant that is particularly useful in analytical chemistry. Common organic hypervalent iodine reagents such as (dichloroiodo)benzene and (diacetoxyiodo)benzene are occasionally used in chemical industry as the reagents for production of important pharmaceutical intermediates. Iodonium salts have found industrial application as photoinitiators for cationic photopolymerizations. Various iodonium compounds are widely used as precursors to [18F]-fluorinated radiotracers in the Positron Emission Tomography (PET).

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

“…Through an umpolung process driven by PIDA and MX (LiCl, LiBr, CuI), the selective synthesis of 3-halogenated quinolin-2-ones (188) from N-arylpropynamides (187) was achieved, as reported by Du et al [145] This procedure produced 3-halogenated quinolin-2-ones with great selectivity, in contrast to most prior electrophilic cyclization/halogenation processes that produced spiro [4,5]trienones (Scheme 65).…”

“…Since then, the demand for iodine organic compounds has skyrocketed. In organic synthesis, hypervalent iodine reagents are extensively used as oxidants and electrophilic reagents [1–16] . In general, three typical reactivity patterns for hypervalent iodine reagents have been observed: (i) ligand exchange, (ii) reductive elimination, and (iii) ligand coupling.…”

“…In organic synthesis, hypervalent iodine reagents are extensively used as oxidants and electrophilic reagents. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] In general, three typical reactivity patterns for hypervalent iodine reagents have been observed: (i) ligand exchange, (ii) reductive elimination, and (iii) ligand coupling. Under the right conditions, hypervalent iodine reagents exhibit radical type reactions, homolytic reactions, and single-electron transfer (SET) reactions.…”

Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis

“…On the other hand, quinoxalin-2(1H)-ones are widely present in a variety of pharmacologically active molecules and naturally occurring chemicals, making them a valuable class of heterocycles. The decarboxylative alkylation of quinoxalin-2(1H)-ones (2) with phenyliodine(III) dicarboxylates under visible light was established by He and co-workers, as an effective and sustainable method for producing 3-alkylquinoxalin-2(1H)-ones (3 and 4) in the presence of PIDA (1) and PEG-200 as solvent (Scheme 1) [15]. Due to the importance of alkyl groups in the life and material sciences, alkylation reactions to create alkylated heterocycles have garnered the attention of chemists as a key area of research.…”

“…In comparison to conventional heavy-metal oxidants, hypervalent iodine (III) reagents, also known as "3-iodanes", have attracted a lot of attention over the past three decades because they are plentiful, stable, non-toxic, environmentally friendly, and mild 2e − oxidants with a variety of applications [1][2][3][4][5][6]. They consistently support distorted trigonal bipyramidal geometry with the electronegative ligands in the axial positions and the less electronegative aryl ring and two lone pairs of electrons in the equatorial positions.…”