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Updated: Aug 3, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-catalyzed remote meta-C-H olefination of cinnamates
Manickam Bakthadoss1, Mir Ashiq Hussain1, Tadiparthi Thirupathi Reddy1
1Department of Chemistry, Pondicherry University, Puducherry 605014, India. bhakthadoss@yahoo.com.
Abstract:
The palladium-catalyzed remote meta-C-H olefination of geometrically challenging substituted cinnamates using a nitrile directing group derived from 2-cyanobenzoic acid has been described. This new protocol is applicable to various olefin coupling partners and provides the corresponding meta-olefinated products in very good yields and with high selectivity. In addition, using this methodology, a variety of acrylates with tethered bioactive molecules, such as naphthoquinone, methyl salicylate, paracetamol, thymol, sesamol, chalcone, naproxen, cholesterol and estrone, have been coupled to produce the desired meta-olefinated products.
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