Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

He Huang, Zack M. Strater, Tristan H. Lambert*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

155 Citations (Scopus)

Abstract

The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

Original languageEnglish
Pages (from-to)1698-1703
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number4
DOIs
Publication statusPublished - 29 Jan 2020
Externally publishedYes

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Huang, H., Strater, Z. M., & Lambert, T. H. (2020). Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity. Journal of the American Chemical Society, 142(4), 1698-1703. https://doi.org/10.1021/jacs.9b11472