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Updated: Feb 5, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters
Nicholas W M Michel1, Alexandria D M Jeanneret1, Hyehwang Kim1
1Davenport Research Laboratories, Department of Chemistry , University of Toronto , 80 St George Street , Toronto , Ontario , M5S 3H6 , Canada.
Abstract:
A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.
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