Synthesis of Polymeric Diaryliodonium Salts and Its Use in Preparation of Diaryl Sulfides and Diaryl Ethers

Diaryliodonium Salts: A Journey from Obscurity to Fame

“…[14] Polymer-supported diaryliodonium salts have recently been prepared from the corresponding (diacetoxyiodo)arenes in this manner. [17,18] The first regiospecific synthesis of diaryliodonium tosylates was discovered by Koser and co-workers in 1980. The reaction of hydroxy(tosyloxy)iodobenzene (PhI(OH)OTs, Kosers reagent) with arylsilanes under neutral conditions occurred at the ipso-position regardless of substituents (Scheme 4 b).…”

“…[147] Polymer-supported diaryliodonium salts have been used to prepare diaryl ethers and thioethers in moderate to good yields by reaction with either sodium aryloxides or arylthiolates. [18] In 1975, a detailed investigation into the reaction of diaryliodonium salts with sodium alkoxides was published by McEwen and co-workers. [148] It was found that treatment of diphenyliodonium tetrafluoroborate with sodium ethoxide in ethanol for 90 min yielded four products (Scheme 38).…”

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

“…[14] Polymergebundene Diaryliodoniumsalze wurden kürzlich aus den entsprechenden (Diacetoxyiod)arenen auf diese Weise hergestellt. [17,18] Die erste regiospezifische Synthese von Diaryliodoniumtosylaten wurde von Koser und Mitarbeitern in den 80er Jahren entdeckt. Die Reaktion von Hydroxy(tosyloxy)iodbenzol (PhI(OH)OTs, Koser-Reagens) mit Arylsilanen unter neutralen Bedingungen fand ungeachtet der Substituenten an der ipso-Position statt (Schema 4 b).…”

“…-arylthiolaten zu synthetisieren. [18] 1975 veröffentlichten McEwen und Mitarbeiter eine detaillierte Studie der Reaktion von Diaryliodoniumsalzen mit Natriumalkoxiden. [148] Bei 90-minütiger Umsetzung von Diphenyliodoniumtetrafluorborat mit Natriumethoxid in Ethanol wurden vier Produkte erhalten (Schema 38).…”

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

“…In 2001, Huang et al reported the preparation of diaryl sulfides (36) using benzenethiolates (35) and polymer bounded diaryliodonium salts. 32 The synthesis of different diaryl ethers was also achieved using sodium phenolate derivatives as starting materials. The reactions were performed in dimethylformamide at 100 °C (Scheme 17) and various diaryl sulfides were isolated in 67-76% yield.…”