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

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.