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Updated: Jun 11, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rh catalyzed olefination and vinylation of unactivated acetanilides
Frederic W Patureau1, Frank Glorius
1Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
Abstract:
In the catalyzed oxidative olefination of acetanilides (oxidative-Heck coupling), Rh offers great advantages over more common Pd catalysts. Lower catalyst loadings, large functional group tolerance (in particular to halides), and higher reactivity of electron-neutral olefins (styrenes) are some of the attractive features. Most interestingly, even ethylene reacts to yield the corresponding acetanilido-styrene. Moreover, the Cu(II) oxidant can also be utilized in catalytic amounts with air serving as the terminal oxidant.
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