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Updated: Sep 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd-Catalyzed γ-Acetoxylation of Alkylamides: Structural Influence of Directing Groups
Peng-Yu Liu1,2, Shi-Chen Zhao2, Ming-Yuan Zhang2
1Key Laboratory for Functional Material, Educational Department of Liaoning Province, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, China.
Abstract:
Although direct acetoxylation and cyclization of alkylamide have been extensively reported, investigation of the structural influence of directing groups on selectivity is limited. Pd-catalyzed 2-methoxyiminoacyl (MIA) assisted γ-acetoxylation of alkylamides has been developed. Further DFT studies have demonstrated that the directing groups have a significant influence on the reductive elimination step. The strong electron-donating effect of the OMe group in MIA leads to the preferential formation of a five-membered cyclopalladium (OAc-Pd-C) complex, which favors the acetoxylation pathway.
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