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Updated: Sep 5, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation
Thomas Rossolini1, Ashis Das1, Stefano Nicolai1
1Laboratory of Catalysis and Organic Synthesis and National Centre of Competence in Research Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne, EPFL, 1015 Lausanne, Switzerland.
Abstract:
A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturated carbon-carbon bonds was achieved under oxidative conditions, most probably via high-valent Pd intermediates. Good yields and high diastereoselectivity were obtained with aryl-substituted alkenes, whereas nonterminal alkyl-substituted olefins gave aza-Heck products. Tether cleavage under mild conditions provided fast access to functionalized β-amino alcohols.
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