Issue 35, 2023

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.

Graphical abstract: Palladium-catalyzed remote meta-C–H olefination of cinnamates

Supplementary files

Article information

Article type
Communication
Submitted
20 jan 2023
Accepted
28 mar 2023
First published
03 apr 2023

Chem. Commun., 2023,59, 5249-5252

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

M. Bakthadoss, M. A. Hussain and T. T. Reddy, Chem. Commun., 2023, 59, 5249 DOI: 10.1039/D3CC00289F

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