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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Synthesis of α-Aryl Secondary Amides via Nickel-Catalyzed Reductive Coupling of Redox-Active Esters
Alexis L Gabbey1, Nicholas W M Michel1, Jonathan M E Hughes2
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Abstract:
The transition-metal-catalyzed α-arylation of secondary amides remains a synthetic challenge due to the presence of a free N-H bond. We report a strategy to synthesize secondary α-aryl amides via a Ni-catalyzed reductive arylation of redox-active N-hydroxyphthalimide (NHP) esters of malonic acid half amides. This transformation proceeds under mild conditions and displays excellent chemoselectivity for amide α-arylation in the presence of other enolizable carbonyls. The NHP ester substrates are readily prepared from Meldrum's acid.
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