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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium catalyzed direct meta-C-H functionalization of aryl acetic esters
Manickam Bakthadoss1, Raj Laxmi Shaw1, Alapati Yaswanth1
1Department of Chemistry, Pondicherry University, Puducherry, 605014, India. bakthadoss@pondiuni.ac.in.
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Herein, we report a palladium(II)-catalyzed direct meta-C-H functionalization of weakly coordinating aryl acetic esters, enabling regioselective olefination with maleimides and naphthoquinone as the coupling partners with good yields and selectivity for the first time. Interestingly, a variety of ibuprofen and naproxen derivatives have been utilized as substrates to couple with naphthoquinone and maleimides. This methodology accommodates acrylate tethered to bioactive motifs such as cholesterol, estrone, paracetamol, and thymol, affording the corresponding meta-olefinated derivatives. Furthermore, the maleimide-coupled products were evaluated for their photophysical properties.
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