Issue 21, 2021

Scalable electrochemical synthesis of diaryliodonium salts

Abstract

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN–HFIP–TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.

Graphical abstract: Scalable electrochemical synthesis of diaryliodonium salts

Supplementary files

Article information

Article type
Paper
Submitted
09 mars 2021
Accepted
04 mai 2021
First published
04 mai 2021
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2021,19, 4706-4711

Scalable electrochemical synthesis of diaryliodonium salts

M. Elsherbini and W. J. Moran, Org. Biomol. Chem., 2021, 19, 4706 DOI: 10.1039/D1OB00457C

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