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Updated: Dec 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Dehydrogenative Coupling of Benzylic and Aldehydic C-H Bonds
Tairin Kawasaki1, Naoki Ishida1, Masahiro Murakami1
1Department of Synthetic Chemistry and Biological Chemistry , Kyoto University , Katsura , Kyoto 615-8510 , Japan.
Abstract:
A photoinduced dehydrogenative coupling reaction between benzylic and aldehydic C-H bonds is reported. When a solution of an alkylbenzene and an aldehyde in ethyl acetate is irradiated with visible light in the presence of iridium and nickel catalysts, a coupled α-aryl ketone is formed with evolution of dihydrogen. An analogous C-C bond forming reaction occurs between a C-H bond next to the nitrogen of an N-methylamide and an aldehydic C-H bond to produce an α-amino ketone. These reactions provide a straightforward pathway from readily available materials leading to valued structural motifs of pharmacological relevance.
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