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. 2022 Jul 25;61(30):e202204088.
doi: 10.1002/anie.202204088. Epub 2022 Jun 9.

Diazaphospholene-Catalyzed Radical Reactions from Aryl Halides

Robert D Riley  1 , Blake S N Huchenski  1 , Karlee L Bamford  1 , Alexander W H Speed  1
Affiliations

Diazaphospholene-Catalyzed Radical Reactions from Aryl Halides

Robert D Riley et al. Angew Chem Int Ed Engl. .

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.

Keywords: Catalysis; Diazaphospholene; Heterocycles; Photochemistry; Radical Addition.

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References

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