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Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.

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 ?-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.

SUBMITTER: Huang H

PROVIDER: S-EPMC7251231 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.

Huang He H Strater Zack M ZM Lambert Tristan H TH

Journal of the American Chemical Society 20200114 4

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 photoex ...[more]

PMID: 31904939

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