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C-C Bond Activation and Demethylenation of Epoxides by Amine Radical Dications

Eric Holt, Nathaniel G. Garrison, Rozhin Rowshanpour, Justin Jeeyoung Kim, Nicolas Henriquez, Winson Lam, Neil Kiame, Jack Williams, Sherrie Zhao, Travis Dudding* and Thomas Lectka*

*Brock University, St. Catharines, Ontario L2S3A1, Canada; Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States, Email:,

E. Holt, N. G. Garrison, R. Rowshanpour, J. J. Kim, N. Henriquez, W. Lam, N. Kiame, J. Williams, S. Zhao, T. Dudding, T. Lectka, J. Org. Chem., 2023, 88, 7597-7600.

DOI: 10.1021/acs.joc.3c00605


A radical-based C-C bond scission of 1,1-disubstituted epoxides followed by demethylenation provides ketones. The reaction is accomplished by Selecfluor and its radical dication working in tandem.

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proposed mechanism

Key Words

ketones, Selectfluor, photochemistry

ID: J42-Y2023