Iodonium Salts Containing Heterocyclic Iodine^1-3

Diaryliodonium Salts: A Journey from Obscurity to Fame

“…[63] Hydrogen peroxide in acetic anhydride/sulfuric acid could be used in the formation of certain heterocyclic diaryliodonium salts, for example, from 2-iodophenyl(phenyl) ether. [64] The next synthesis of acyclic diaryliodonium salts was reported in 1959, when aryl iodides were oxidized in situ with potassium persulfate or barium peroxide, followed by condensation with an arene (Scheme 8 c). [14,65] Diaryliodonium salts with internal carboxylate anions have also been prepared in this way.…”

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

“…[63] Wasserstoffperoxid in Essigsäure-anhydrid/Schwefelsäure bewirkte die Bildung von heterocyclischen Diaryliodoniumsalzen aus 2-Iodphenyl(phenyl)ethern. [64] Die nächste Synthese acyclischer Diaryliodoniumsalze wurde 1959 beschrieben, wobei Aryliodide mit Kaliumpersulfat oder Bariumperoxid in situ oxidiert und anschließend mit einem Aren kondensiert wurden (Schema 8 c). [14,65] Diaryliodoniumsalze mit internen Carboxylat-Anionen wurden ebenfalls auf diese Weise hergestellt.…”

One-Pot Synthesis of Heteroatom-Bridged Cyclic Diaryliodonium Salts

“…In a two-step procedure, the corresponding oxidized iodane was isolated and subsequent cyclization of the oxidized intermediate with sulfuric acid gave the desired cyclic iodonium salts. [6] Modern approaches towards iodaoxinium salts based on preexisting iodinated diarylethers have been described by Wen and Huber. [7][8] Due to the growing interest of these reactive compounds, efficient and reliable procedures for their efficient synthesis are highly desirable.…”