Scalable electrochemical synthesis of diaryliodonium salts

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)4706-4711
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number21
Early online date4 May 2021
DOIs
Publication statusPublished - 7 Jun 2021

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