Scalable electrochemical synthesis of diaryliodonium salts

Elsherbini, Mohamed; Moran, Wesley J.

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.

Citation

Elsherbini, M., & Moran, W. J. (2021). Scalable electrochemical synthesis of diaryliodonium salts. Organic and Biomolecular Chemistry, 19(21), 4706-4711. https://doi.org/10.1039/d1ob00457c

• Journal Article Type: Article
• Acceptance Date: May 4, 2021
• Online Publication Date: May 4, 2021
• Publication Date: 2021
• Deposit Date: Feb 20, 2024
• Publicly Available Date: Feb 27, 2024
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 21
• Pages: 4706-4711
• DOI: https://doi.org/10.1039/d1ob00457c
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2021/ob/d1ob00457c
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Wesley J. Moran (ORCID); : Single-blind; : Received 9 March 2021; Accepted 4 May 2021; Accepted Manuscript published 4 May 2021; Advance Article published 7 May 2021; Version of Record published 2 June 2021