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Updated: May 7, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic allylation of stabilized phosphonium ylides with primary allylic amines
Xian-Tao Ma1, Yong Wang, Rui-Han Dai
1Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
Abstract:
A range of ketone-stabilized phosphonium ylides were allylated with high regioselectivity by primary allylic amines in the presence of 5 mol % Pd(PPh3)4 and 10 mol % B(OH)3, and subsequent one-pot Wittig olefination gave structurally diverse α,β-unsaturated ketones in good to excellent overall yields with excellent E selectivity. The one-pot allylation/olefination reaction was extended to ester- and nitrile-stabilized phosphonium ylides by replacing B(OH)3 with TsOH, and the corresponding α,β-unsaturated esters and nitriles were obtained in moderate overall yields.
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