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Updated: Aug 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Metal-free visible-light-induced hydroxy-perfluoroalkylation of conjugated olefins using enamine catalyst
Koto Tagami1, Yu Ofuji1, Tadashi Kanbara1
1Department of Chemistry, Faculty of Science, Ochanomizu University Otsuka, Bunkyo-ku Tokyo 112-8610 Japan yajima.tomoko@ocha.ac.jp.
Abstract:
We developed a simple and sustainable method for the hydroxy-perfluoroalkylation of electron-deficient conjugated olefins and styrenes. In this protcol, in situ generated enamine forms electron-donor-accepter (EDA) complexes with perfluoroalkyl iodide, and reaction proceed with visible-light irradiation. Tertiary amine also interacts with perfluoroalkyl iodide via halogen-bonding, promoting the perfluoroalkyl radical generation. This reaction does not require any transition-metal or photoredox catalyst, and gaseous oxygen is used as the green hydroxy source. Moreover, various commercially available substrates and perfluoroalkyl iodides were tolerated, affording the desired hydroxy-perfluoroalkylated products in good to moderate yields (>50 examples, up to 90%).
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