4.7 Article

Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2H-azirines with (Diacetoxy)iodobenzene

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11735-11740

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01625

Keywords

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Funding

  1. DST-RSF Major Research Project [INT/RUS/RSF/P-08]
  2. Russian Science Foundation -Russia [18-73-00301]
  3. Russian Science Foundation [18-73-00301] Funding Source: Russian Science Foundation

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A visible-light-promoted regioselective coupling of C(sp(3))-H of aryl-2H-azirine and (diacetoxy)-iodobenzene has been reported. Rose Bengal as an organo-photoredox catalyst has been used in this reaction. The reaction proceeds under aerobic condition at room temperature. A variety of aryl-2H-azirines gives the corresponding acyloxylated azirines under this reaction conditions. The reaction goes through a radical pathway. The protocol is also applicable on gram-scale synthesis.

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