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Updated: Sep 22, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Diazaphospholene-Catalyzed Radical Reactions from Aryl Halides
Robert D Riley1, Blake S N Huchenski1, Karlee L Bamford1
1Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Abstract:
Diazaphospholenes are widely used as hydride transfer catalysts, however their use in radical reactions is a recently emerging area. Here, we show prior stoichiometric radical cyclizations of aryl iodides mediated by diazaphospholene hydrides are made catalytic by the combination of phenylsilane and alkali metal salts to regenerate the diazaphospholene hydride. The scope was expanded to include aryl bromides, which benefit from visible light irradiation. Twenty one substrates underwent cyclization, including a dearomative cyclization. Extension to six intermolecular radical hydroarylations with arenes, thiophenes, and a pyridine was also accomplished.
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