Selective multi-electron aggregation at a hypervalent iodine center by sequential disproportionation. Issue 29 (20th March 2023)

• Record Type: Journal Article
• Authors: Thai, Phong; Frey, Brandon L.; Figgins, Matthew T.; Thompson, Richard R.; Carmieli, Raanan; Powers, David C.
• Is Part Of: Chemical communications. Volume 59:Issue 29(2023)
• Page Start: 4308
• Page End: 4311
• Publication Date: 2023-03-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d3cc00549f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We report a strategy to aggregate two- or four interfacial electron transfers at an iodine center as an approach to multi-electron electrosynthesis. The intermediates are characterized via UV-vis spectroscopy and single crystal X-ray crystallography. Abstract : We demonstrate that sequential disproportionation reactions can enable selective aggregation of two- or four electron–holes at a hypervalent iodine center. Disproportionation of an anodically generated iodanyl radical affords an iodosylbenzene derivative. Subsequent iodosylbenzene disproportionation can be triggered to provide access to an iodoxybenzene. These results demonstrate multielectron oxidation at the one-electron potential by selective and sequential disproportionation chemistry.