Synthesis of Poly-nitrile Aromatics via Palladium-Catalyzed Cyanation of Aryl Bromides with Potassium Hexacyanoferrate(II)

Abstract

Modification of Beller's palladium-catalyzed cyanation procedure leads to a versatile and rapid route to poly-nitrile aromatics via easily available aryl bromides that improve on known literature methods. All cyanide ions on the iron(II) center of the nontoxic cyanide source [potassium hexacyanoferrate(II)] can be transferred to the aryl halide using palladium(II) acetate and 1,1′-bis(diphenylphosphino)ferrocen (dppf).

Keywords:

• Aryl bromide
• catalysis
• cyanation
• palladium-catalyzed
• potassium hexacyanoferrate(II)

Notes

^a General conditions: aryl halide (1 equiv), K₄[Fe(CN)₆] (0.25 equiv per halide substituent), additive (1 equiv), catalyst, ligand, 10 ml solvent, 120 °C, 10 h.

^b isolated yields.