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 language | English |
---|---|
Pages (from-to) | 1698-1703 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 142 |
Issue number | 4 |
DOIs | |
Publication status | Published - 29 Jan 2020 |
Externally published | Yes |
Fingerprint
Dive into the research topics of 'Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity'. Together they form a unique fingerprint.Cite this
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