4.7 Article

Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 13, Pages 3499-3505

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00412g

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Funding

  1. Natural Science Foundation of China [22101070]
  2. Hebei Natural Science Foundation [B2021201015, B2019201415]
  3. Advanced Talents Incubation Program of Hebei University [521100221004]

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The study demonstrates a mild and efficient method for the construction of indoles using 4-CzIPN as a photocatalyst and alpha-fluoro-beta-enamino esters as substrates under visible light irradiation. Mechanistic studies reveal that the formation of indoles is attributed to the triplet N-aryl enamines produced through energy transfer.
Using 4-CzIPN as an energy transfer (EnT) photocatalyst and alpha-fluoro-beta-enamino esters as substrates, a mild 6 pi-photocyclization/defluorination of N-aryl enamines was carried out to efficiently construct indoles without an oxidant and a transition metal catalyst under visible light irradiation. Mechanistic studies reveal that the triplet N-aryl enamines produced through energy transfer from the excited 4-CzIPN* are responsible for the formation of indoles.

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