Diaryliodonium Salts: Structures and Synthesis

Abstract

: Due to similar reactivity in comparison with aromatic organometallic reagents, diaryliodonium salts are currently in broad usage as less toxic, highly efficient, stable and mild electrophilic reagents in organic synthesis. The hypervalent iodine center of diaryliodonium salts can lead to unique reactivity, which thus is frequently presented in metal-free arylations or metal-involved elementary reactions such as oxidative addition, reduction elimination, ligand coupling and ligand exchange reaction. As such, diaryliodonium salts have experienced explosive growth by transferring aromatics to the target molecules. In contrast to the reviews on the synthetic utility or aryl transformations by using diaryliodonium salts, this review provides a summary of their structures and the synthetic strategies towards them during recent decades.

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

“…These compounds have numerous applications for example, they are used as vital building blocks in organic synthesis, polymerizations besides participating in biologically active molecules. [480][481][482] Soldatova et al reported a facile one-pot synthesis for symmetrically as well as unsymmetrically substituted diaryliodonium trifluoroactetates 701 a-k anddiaryliodonium triflates 702 l-r from arenes 700 and aryl iodides 699 using oxone as a cheap stoichiometric oxidant (Scheme 212). [483] In another study, they have also reportedbis-aryliodonium salts 705 a-m from arenes 704 and aryl iodides 703 in the presence of oxone-sulfuric acid and aq.…”

“…Diaryliodonium salts are vastly inspected compounds in organic synthesis which are generally produced from the corresponding iodoarenes by means of oxidative protocols. These compounds have numerous applications for example, they are used as vital building blocks in organic synthesis, polymerizations besides participating in biologically active molecules [480–482] . Soldatova et al .…”

Hypervalent Iodonium Zwitterions and Nucleophilic Aromatic Substitution: A Multiple-Step Experiment in Organic Chemistry

“…HIC are characterized by a three-center-four-electron bond (L-I-L) in which the 5p orbital on iodine overlaps with orbitals on two ligands. These orbitals display a reactivity reminiscent of that of transition-metal reagents with respect to ligand exchange, oxidative addition, reductive elimination, and ligand coupling . The synthetic potential and extraordinary character of HIC are, however, still widely underestimated; therefore, this article aims to attract the attention of fellow scientists and university students to the benefits of HIC .…”

Introduction to hypervalent iodine chemistry. Part 3

“…Aryliodonium salts have attracted significant interest as electrophilic arylating reagents. 37,43 Hypervalent iodine organosulfonates have found wide application as powerful electrophiles and oxidizing reagents. 23,31,61 The development of new synthetic methodologies and the use of hypervalent iodine reagents in specific classes of reactions have attracted significant research activity.…”