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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
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Original Articles

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

, &
Pages 1042-1051 | Received 03 Feb 2010, Published online: 03 Mar 2011
 

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).

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.

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