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An expedient Pd/DBU mediated cyanation of aryl/heteroaryl bromides with K4[Fe(CN)6].

Chemical communications (Cambridge, England) (2012-02-07)
Dengyou Zhang, Haifeng Sun, Lei Zhang, Yu Zhou, Chunpu Li, Hualiang Jiang, Kaixian Chen, Hong Liu
RESUMEN

A practical Pd(PPh(3))(4)/DBU catalytic system for the synthesis of pharmaceutically relevant aminopyridine nitrile intermediates, as well as a variety of other aryl nitriles using non-toxic K(4)[Fe(CN)(6)] has been developed. The key features of our new protocol for cyanation lie in that the reaction can be carried out with readily available Pd(PPh(3))(4) under mild and green conditions, even without the assistance of other ligands.

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Sigma-Aldrich
1,8-Diazabiciclo[5.4.0]undec-7-eno, 98%
Sigma-Aldrich
1,8-Diazabicyclo[5.4.0]undec-7-ene, puriss., ≥99.0% (GC)
Sigma-Aldrich
2-Amino-3-bromopyridine, 97%