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

In this note, we explore a unique reactivity pattern that involves a rare radical-based C-C bond scission of epoxides followed by demethylenation. The reaction is accomplished by Selecfluor and its radical dication working in tandem; a mechanism supported by experiment and DFT calculations is proposed that involves the generation and identification of a key reactive intermediate. The reaction seems to be fairly general for 1,1-disubstituted epoxides.

Citation

Eric Holt, Nathaniel G Garrison, Rozhin Rowshanpour, Justin Jeeyoung Kim, Nicolas Henriquez, Winson Lam, Neil Kiame, Jack Williams, Sherrie Zhao, Travis Dudding, Thomas Lectka. C-C Bond Activation and Demethylenation of Epoxides by Amine Radical Dications. The Journal of organic chemistry. 2023 Jun 02;88(11):7597-7600

PMID: 37159569

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