Low-Cost, Safe, and Anion-Flexible Method for the Electrosynthesis of Diaryliodonium Salts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43930159" target="_blank" >RIV/60461373:22310/24:43930159 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/10.1021/acs.joc.4c01521" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.joc.4c01521</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.4c01521" target="_blank" >10.1021/acs.joc.4c01521</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Low-Cost, Safe, and Anion-Flexible Method for the Electrosynthesis of Diaryliodonium Salts

Popis výsledku v původním jazyce

An electrochemical approach toward the synthesis of diaryliodonium salts based on anodic C-I coupling between aryl iodides and arenes is presented. In contrast to previous protocols, our method requires no chemical oxidants, strong acids, or fluorinated solvents. A further advantage is that by use of the appropriate supporting electrolyte, the counterion of choice can be introduced, which is time- and cost-saving as compared to postsynthesis ion exchange. This &quot;anion-flexibility&quot; is particularly interesting when considering the pronounced effect of the counterion on the reactivity of diaryliodonium species in aryl transfer reactions. The scope of our method comprises 24 examples with isolated yields of up to 99%. Scalability was demonstrated by the synthesis on a gram scale. Furthermore, it was shown that the diaryliodonium-containing post-electrolysis solution can be used without further workup as a reactive medium for O-arylation reactions. Finally, a series of para-substituted diaryliodonium compounds was studied using linear sweep voltammetry on a microelectrode and analyzed with respect to the influence of the electronic structure on the redox behavior.

Název v anglickém jazyce

Low-Cost, Safe, and Anion-Flexible Method for the Electrosynthesis of Diaryliodonium Salts

Popis výsledku anglicky

An electrochemical approach toward the synthesis of diaryliodonium salts based on anodic C-I coupling between aryl iodides and arenes is presented. In contrast to previous protocols, our method requires no chemical oxidants, strong acids, or fluorinated solvents. A further advantage is that by use of the appropriate supporting electrolyte, the counterion of choice can be introduced, which is time- and cost-saving as compared to postsynthesis ion exchange. This &quot;anion-flexibility&quot; is particularly interesting when considering the pronounced effect of the counterion on the reactivity of diaryliodonium species in aryl transfer reactions. The scope of our method comprises 24 examples with isolated yields of up to 99%. Scalability was demonstrated by the synthesis on a gram scale. Furthermore, it was shown that the diaryliodonium-containing post-electrolysis solution can be used without further workup as a reactive medium for O-arylation reactions. Finally, a series of para-substituted diaryliodonium compounds was studied using linear sweep voltammetry on a microelectrode and analyzed with respect to the influence of the electronic structure on the redox behavior.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)

Projekt

<a href="/cs/project/EF16_025%2F0007445" target="_blank" >EF16_025/0007445: Baterie na bázi organických redoxních látek pro energetiku tradičních i obnovitelných zdrojů.</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

JOURNAL OF ORGANIC CHEMISTRY

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

89

Číslo periodika v rámci svazku

19

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

14129-14134

Kód UT WoS článku

001318700700001

EID výsledku v databázi Scopus

2-s2.0-85205730286