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Cyclohexylcarbonitriles: diastereoselective arylations with TMPZnClLiCl
Journal article   Peer reviewed

Cyclohexylcarbonitriles: diastereoselective arylations with TMPZnClLiCl

Robert J Mycka, Stephanie Duez, Sebastian Bernhardt, Johannes Heppekausen, Paul Knochel and Fraser F Fleming
Journal of organic chemistry, Vol.77(17), p7671
07 Sep 2012

Abstract

Analysis Arylation Bromides Catalysis Chemical properties Nitriles Structure Thermal properties
Deprotonating substituted cyclohexanecarbonitriles with TMPZnCl*LiCl is used to generate zincated nitriles that diastereoselectively couple with aryl bromides in the presence of catalytic Pd[(OAc).sub.2] and S-Phos. The unusual diastereoselectivity trends observed for the generated nitriles could have important implication for synthesizing substituted cyclohexanecarbonitrile-containing pharmaceuticals.

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