Ligand-Enabled Reactivity and Selectivity in a Synthetically Versatile Aryl C–H Olefination

Abstract

Heck of an Alternative: The Mizoroki-Heck reaction is widely used in organic synthesis to link together unsaturated carbon fragments such as olefins and arenes. However, one of its drawbacks is the need to append a reactive group such as a halogen to one of the reagents beforehand. Wang et al. (p. 315 , published online 26 November) present an alternative palladium-catalyzed reaction that links olefins directly to aryl acids. Oxygen added to the reaction medium concurrently oxidizes the aryl C-H bond at the linkage site, eliminating the need for prior halogenation. Introducing amino acid–derived ligands tunes the aryl site at which the reaction takes place, and efficient reactivity can be achieved across a diverse range of substrates.