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Updated: Sep 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium(II)/Lewis Acid-Catalyzed Olefination of Arylacetamides with Dioxygen
Miao Zeng1, Hongwu Jiang1, Kaiwen Li1
1School of Chemistry and Chemical Engineering, Key Laboratory of Material Chemistry for Energy Conversion and Storage (Huazhong University of Science and Technology), Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, P. R. China.
Abstract:
The present work introduces Pd(II)/LA-catalyzed (LA: Lewis acid) olefination of arylacetamides with dioxygen as the oxidant source. This protocol tolerates with different functional groups on the substrates, and the catalytic efficiency is highly Lewis acidity-dependent on added LA, that is, a stronger LA provided a better promotional effect. The 1H NMR studies of the semireaction between the arylacetamide and the Pd(II)/Sc(III) catalyst in HOAc-d4 disclosed the formation of a palladacycle intermediate, and the C-H activation step was reversible, which led to the formation of the deuterated arylacetamide substrate and the palladacycle intermediate. Further semireaction between the palladacycle intermediate and the olefin disclosed that it was a clean and much faster reaction than the C-H activation step, thus revealing multiple mechanistic information for Pd(II)-catalyzed C-H activation.
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