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Palladium-catalyzed remote meta-C-H olefination of cinnamates.

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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… Click to show full 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.

Keywords: palladium catalyzed; meta olefination; catalyzed remote; remote meta

Journal Title: Chemical communications
Year Published: 2023

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