Details

Autor(en) / Beteiligte

• Riley, Robert D.
• Huchenski, Blake S. N.
• Bamford, Karlee L.
• Speed, Alexander W. H.

Titel

Diazaphospholene‐Catalyzed Radical Reactions from Aryl Halides

Ist Teil von

• Angewandte Chemie International Edition, 2022-07, Vol.61 (30), p.e202204088-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Diazaphospholene radical chemistry has been made catalytic with a combination of carbonates and phenylsilane as a terminal reductant. The system is suitable for generation of aryl radicals and intermolecular and intramolecular addition of these radicals.